Supplementary Material

2-(3’,5’-dibromo-2’-methoxyphenoxy)-3,5-dibromophenol (1): 1H NMR (CDCl3, 300 MHZ) d 7.48 (1H, d, J = 2.2 Hz, H-4’), 7.38 (1H, d, J = 2.2 Hz, H-4), 7.21 (1H, d, J = 2.2 Hz, H-6), 6.83 (1H, d, J = 2.2 Hz, H-6’), 5.34 (1H, brs, OH), 4.06 (3H, s, OCH3); 1H NMR (acetone-d6, 400 MHz) d 7.45 (1H, d, J = 2.3 Hz, H-4’), 7.41 (1H, d, J = 2.2 Hz, H-4), 7.26 (1H, d, J = 2.2 Hz, H-6), 6.71 (1H, d, J = 2.3 Hz, H-6’), 4.00 (3H, s, OCH3); 13C NMR (acetone-d6, 100 MHz) C-, 139.1 (C-2), 119.5 (C-3), 127.0 (C-4), 118.9 (C-5), 120.9 (C-6), 152.4 (C-1’), 146.6 (C-2’), 119.9 (C-3’), 129.3 (C-4’), 116.9 (C-5’), 117.5 (C-6’), 61.1 (OCH3); APCI [M – H]- m/z 527.3 (9), 529.1 (63), 531.0 (100), 532.9 (62), 534.9 (12).

2-(3’,5’-dibromo-2’-hydroxyphenoxy)-3,4,5,6-tetrabromophenol (2): 1H NMR (CDCl3, 300 MHZ) d 7.45 (1H, d, J = 2.2 Hz, H-4’), 6.68 (1H, d, J = 2.2 Hz, H-6’), 6.04 (1H, s, OH), 6.01 (1H, s, OH); ); 1H NMR (acetone-d6, 400 MHz) d 7.41 (1H, d, J = 2.2 Hz, H-4’), 6.85 (1H, d, J = 2.2 Hz, H-6’); 13C NMR (acetone-d6, 100 MHz) 05C-, 140.6 (C-2), 119.3 (C-3), 121.6 (C-4), 127.2 (C-5), 116.5 (C-6), 146.9 (C-1’), 145.3 (C-2’), 112.2 (C-3’), 130.4 (C-4’), 111.7 (C-5’), 117.1 (C-6’); APCI [M – H]- m/z 668.8 (4), 670.7 (27), 672.7 (74), 674.6 (100), 676.6 (69), 678.6 (26), 680.6 (3), [M – Br]- m/z 589.2 (3), 591.2 (27), 593.1 (60), 595.1 (58), 597.0 (30), 598.9 (5).

2-(3’,5’-dibromo-2’-hydroxyphenoxy)-3,5,6-tribromophenol (3): 1H NMR (CDCl3, 300 MHZ) d 7.61 (1H, s, H-4), 7.47 (1H, d, J = 2.5 Hz, H-4’), 6.68 (1H, d, J = 2.5 Hz, H-6’), 6.05 (brs, OH); 1H NMR (acetone-d6, 400 MHz) d 7.64 (1H, s, H-4), 7.40 (1H, d, J = 2.2 Hz, H-4’), 6.74 (1H, d, J = 2.2 Hz, H-6’); 13C NMR (acetone-d6, 100 MHz) 15C-, 139.9 (C-2), 117.5 (C-3), 128.5 (C-4), 124.0 (C-5), 115.5 (C-6), 147.1 (C-1’), 145.3 (C-2’), 112.2 (C-3’), 130.3 (C-4’), 111.7 (C-5’), 117.0 (C-6’); APCI [M – H]- m/z 591.0 (3), 592.8 (60), 594.8 (99), 596.8 (100), 598.6 (51), [M – Br]- m/z 511.1 (3), 513.3 (36), 515.1 (66), 517.1 (49), 519.3 (5).

2-(3’,5’-dibromo-2’-methoxyphenoxy)-3,5,6-tribromophenol (4): 1H NMR (CDCl3, 300 MHZ) d 7.58 (1H, s, H-4), 7.46 (1H, d, J = 2.5 Hz, H-4’), 6.72 (1H, d, J = 2.5 Hz, H-6’), 4.05 (3H, s, OCH3); 1H NMR (acetone-d6, 400 MHz) d 7.65 (1H, s, H-4), 7.48 (1H, d, J = 2.2 Hz, H-4’), 6.82 (1H, d, J = 2.2 Hz, H-6’); 13C NMR (acetone-d6, 100 MHz) 15C-, 139.8 (C-2), 117.6 (C-3), 128.7 (C-4), 124.0 (C-5), 115.8 (C-6), 152.6 (C-1’), 147.2 (C-2’), 120.1 (C-3’), 130.4 (C-4’), 117.6 (C-5’), 118.2 (C-6’); APCI [M – H]- m/z 605.3 (8), 607.3 (47), 609.0 (100), 610.9 (95), 612.8 (45), 614.8 (10).

2-(3’,5’-dibromo-2’-methoxyphenoxy)-3,4,5,6-tetrabromophenol (5): 1H NMR (acetone-d6, 400 MHz) d 7.53 (1H, d, J = 2.2 Hz, H-4’), 6.93 (1H, d, J = 2.2 Hz, H-6’); APCI [M – H]- m/z 684.8 (28), 686.9 (78), 688.9 (100), 690.9 (84), 692.9 (29).

2-(3’,5’-dibromo-2’-hydroxyphenoxy)-3,4,5-tribromophenol (6): 1H NMR (CDCl3, 300 MHZ) d 7.49 (1H, s, H-6), 7.43 (1H, d, J = 2.0 Hz, H-4’), 6.65 (1H, d, J = 2.0 Hz, H-6’); 1H NMR (acetone-d6, 400 MHz) d 7.49 (1H, s, H-6), 7.38 (1H, d, J = 2.2 Hz, H-4’), 6.73 (1H, d, J = 2.2 Hz, H-6’); 13C NMR (acetone-d6, 100 MHz) 16C-, 140.7 (C-2), 118.2 (C-3), 123.0 (C-4), 122.6 (C-5), 122.3 (C-6), 146.7 (C-1’), 144.9 (C-2’), 111.7 (C-3’), 129.8 (C-4’), 111.3 (C-5’), 116.7 (C-6’); APCI [M – H]- m/z 593.2 (11), 595.2 (100), 596.9 (83), 598.7 (44), 600.7 (7).

2-(4’,5’,6’-tribromo-2’-methoxyphenoxy)-4,6-dibromophenol (7): 1H NMR (acetone-d6, 400 MHz) d 7.64 (1H, s, H-3’), 7.39 (1H, d, J = 2.2 Hz, H-5), 6.71 (1H, d, J = 2.2 Hz, H-3), 3.76 (3H, s, OCH3); 13C NMR (acetone-d6, 100 MHz) 451C-, 147.6 (C-2), 117.2 (C-3), 111.6 (C-4), 130.1 (C-5), 112.0 (C-6), 142.2 (C-1’), 154.0 (C-2’), 119.0 (C-3’), 119.5 (C-4’), 1231.5 (C-5’), 119.6 (C-6’), 60.0 (OCH3); APCI [M – H]- m/z 605.0 (10), 607.0 (42), 608.9 (100), 610.9 (95), 612.8 (45), 614.8 (8).

2-(4’,6’-dibromo-2’-methoxyphenoxy)-4,6-dibromophenol (8): 1H NMR (acetone-d6, 400 MHz) d 7.49 (1H, d, J = 2.2 Hz, H-5’), 7.39 (1H, d, J = 2.2 Hz, H-3’), 7.38 (1H, d, J = 2.2 Hz, H-5), 6.62 (1H, d, J = 2.2 Hz, H-3), 3.77 (3H, s, OCH3); 13C NMR (acetone-d6, 100 MHz) 452C-, 147.6 (C-2), 117.2 (C-3), 111.5 (C-4), 129.9 (C-5), 111.9 (C-6), 141.1 (C-1’), 155.3 (C-2’), 117.8 (C-3’), 120.7 (C-4’), 128.3 (C-5’), 119.3 (C-6’), 57.8 (OCH3); APCI [M – H]- m/z 527.1 (4), 529.2 (63), 531.0 (100), 533.0 (70), 534.9 (8).