3-BROMO-2-METHOXYBENZALDEHYDE

K2C03 (13.51 g, 97.75 mmol) and CH3I (2.43 mL, 39.1 mmol) were added to a sol. of 3-bromo-2-hydroxybenzaldehyde (6.55 g, 32.58 mmol) in DMF (164 mL). The r.m. was stirred at r.t. for 18 h. The mixture was poured into a 1 N HCl sol. and the aq. layer was extracted with EtOAc. The o.l. was separated, dried (MgS04), filtered and concentrated in vacuo. Yield: 7 g of intermediate 25 (99percent yield) as a brown-orange oil.To a solution of 3-bromo-2-hydroxy- benzaldehyde (2.72 g, 13.53 mmol) in DMF (70 mL) were added potassium carbonate (5.61 g, 40.59 mmol) and iodomethane (1.01 ml_, 16.24 mmol). The reaction mixture was stirred at RT. After 18 h, the mixture was acidified with cooling using 1 M HCI (aq), extracted with EtOAc. The organic extract was dried (Na3-Bromo-2-hydroxybenzaldehyde (5.0 g, 24.87 mmol) was dissolved in acetone (200 ml) and treated with iodomethane (5.3 g, 37.34 mmol) and potassium carbonate (5.2 g, 37.63 mmol). The mixture was heated to 60° C for 2 hr then cooled to room temperature and filtered. The filtrate was concentrated to dryness and re-dissolved in ethyl acetate. The solution was washed with saturated aqueous sodium bicarbonate and dried over MgSOBu4NOH (40 wtpercent in H2O; 11.1 mL, 16.9 mmol), NaOH (1.15 g, 28.8 mmol), and MeI (2.64 mL, 42.4 mmol) were added to a solution of 3-bromosalicylaldehyde (10) (1.70 g, 8.46 mmol) in CH2Cl2 (60 mL) and water (60 mL). The mixture was vigorously stirred at r.t. for 16 h under air. The layers were separated, the aqueous layer was extracted with CH2Cl2, the combined organic layers were dried (Na2SO4), and the solvent was evaporated. Purification of the residue by flash chromatography (silica gel, isohexane-EtOAc, 15:1) provided methyl ether 11 as a colorless solid; yield : 1.60 g (7.44 mmol, 88percent); mp 30-32 °C. IR (ATR): 3339, 3068, 3012, 2954, 2889, 2826, 2750, 2057, 1679, 1654, 1584, 1447, 1418, 1387, 1233, 1165, 1115, 1069, 986, 851, 801, 779, 747, 699 cm-1. 1H NMR (500 MHz, CDCl3): δ = 3.99 (s, 3 H), 7.14 (td, J = 7.8, 0.7 Hz, 1H), 7.80-7.82 (m, 2 H), 10.36 (d, J = 0.7 Hz, 1H). 13C NMR and DEPT (125 MHz, CDCl3): δ = 63.51 (CH3), 118.20 (C), 125.78 (CH), 127.87 (CH), 130.95 (C), 139.50 (CH), 160.13 (C), 189.14 (CHO). MS (EI): m/z (percent) = 216 (68), 214 (67, [M+]), 198 (95), 196 (81), 185 (25), 184 (23), 183 (17), 182 (23), 170 (38), 168 (24), 145 (35), 143 (35), 119 (35), 92 (43), 77 (78), 63 (100), 50 (34), 38 (18). Anal. Calcd for C8H7BrO2: C, 44.68; H, 3.28. Found: C, 44.87; H, 3.17.

Molecular Weight:215.04
XLogP3:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:213.96294
Monoisotopic Mass:213.96294
Topological Polar Surface Area:26.3
Heavy Atom Count:11
Complexity:138
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes