Phenol, 3-bromo-, 1-acetate

Intermediate 1; 3-Bromophenyl acetate.;To a cold (ice bath) solution of 3-bromophenol (150 g, 867 tnmol) and pyridine (70.0 mL, 867 mmol) in CHExample 14c Compound 15-1 (0412) To a stirred suspension of 3-bromophenol (50 g, 0.29 mol) in pyridine (200 mL) and dichloromethane (100 mL) was added dropwise acetyl chloride (25 mL, 0.35 mol) at 0° C. and the mixture was stirred 18 h at room temperature. LC-MS showed that the reaction was complete. Pyridine and dichloromethane was evaporated in vacuo. Water (600 mL) was added and acidified with hydrochloric acid at pH 2. The reaction mixture was extracted with ethyl acetate (500 mL×3) and the organic phase was dried over anhydrous sodium sulfate, filtrated, concentrated and purified by column chromatography (PE:EA=60:1) to afford compound 15-1 as a colorless liquid (46 g, 74percent).Intermediate 9: (R)-2-(4-bromo-2-methoxyphenyl)propan-l-ol; Intermediate 9A:; [00216] Sulfuric acid (0.3 mL, 5.63 mmol) was added to a well stirred mixture of 3-bromophenol (26.2 g, 152 mmol) and acetic anhydride (15.3 mL, 162 mmol), cooled with a rt water bath. After 30 min, the volatiles were removed on a rotovap. Ice was added to the residue, which was then extracted with ether (3x). The combined organic layers were washed with brine, dried (MgSOCommercially available 3-bromophenol (1, 50 g, 0.289 mol) was added to a mixture of AcCompound (7) (10.0 g, 58 mmol) was dissolved in pyridine (30 mL) under ice-bath and was stirred for 30 min. Acetic anhydride (8.3 mL, 88 mmol) was added dropwise into above mixture at the same temperature. The ice-bath was removed after dropping and the mixture was stirred for 2 h. Concentrated HCl and ice-water (300 mL) was added to the above reaction solution to neutralize PH to 7. The mixture was extracted with AcOEt (100 mL * 3). The organic layer was collected and washed with brine and dried over Na

Molecular Weight:215.04
XLogP3:2.4
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:147
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes