Acetyl chloride → Acetic acid 4-bromo-2-(2,2,2-trifluoro-ethyl)-phenyl ester

HRID 859653Notes

Reaction equation

HRID 859653 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(N(CC)CC)C.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([CH2:20][C:21]([F:24])([F:23])[F:22])[CH:14]=1>>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:1](=[O:3])[CH3:2])=[C:15]([CH2:20][C:21]([F:22])([F:23])[F:24])[CH:14]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 587625624-Bromo-2-(2,2,2-trifluoroethyl)phenol

Product 1

HCID 58764074Acetic acid 4-bromo-2-(2,2,2-trifluoro-ethyl)-phenyl esterYield 78.7%

Procedure

Acetyl chloride (0.91 mL, 12.8 mmol) followed by triethylamine (1.8 mL, 12.8 mmol) were added to a stirred solution of 4-bromo-2-(2,2,2-trifluoroethyl)phenol (2.55 g, 10.7 mmol) dissolved in CH2Cl3 (20 mL). The reaction was stirred for 45 mins and then partitioned between 1N HCl and EtOAc. The organic layer was washed with saturated NaHCO3, brine dried over Na2SO4 and concentrated. Purification by flash column chromatography (0% to 20% EtOAc in hexanes) gave the product as a clear oil (2.50 g). LCMS : apci 297 MH+

Workup

  1. custompartitioned between 1N HCl and EtOAc
  2. washThe organic layer was washed with saturated NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (0% to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5ba721cbf6e84a9d999f77478ff67360
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

Loading…