Water → Phenol, 3-bromo-, 1-acetate

HRID 1684868Notes

Reaction equation

HRID 1684868 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Br:5][C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1.N1C=CC=CC=1.O>ClCCl>[C:1]([O:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([Br:5])[CH:7]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 115633-Bromophenol

Product 1

HCID 141946Phenol, 3-bromo-, 1-acetateYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (10.2 mL, 144 mmol) was added in a dropwise manner over 1 h to a cold (ice bath) solution of 3-bromophenol (25 g, 144 mmol) and pyridine (10.8 mL, 144 mmol) in dichloromethane (100 mL), and the reaction was stirred 18 hr at room temperature. Water (150 mL) was added and the organic layer was extracted with dichloromethane. The combined organic layers were washed with 2.5N NaHSO4, 3N NaOH, water, brine, and dried over Na2SO4, and filtered. Concentration gave the 3-bromophenyl acetate as a pink liquid (28 g, 96%). GC-MS data: 214 (M+); 1H NMR (DMSO-d6): 7.37-7.39 (d, 1H), 7.26-7.30 (m, 2H), 7.04-7.07 (t, 1H), 2.30 (s, 3H).

Workup

  1. extractionthe organic layer was extracted with dichloromethane
  2. washThe combined organic layers were washed with 2.5N NaHSO4, 3N NaOH, water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationConcentration

Sources & evidence

ORD record
ord-7f3d9fa767e4463c84c84876e92be5e4
Source dataset
uspto-grants-2012_04
Patent number
US08147818B2

Reaction notes

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