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

HRID 1438234Notes

Reaction equation

HRID 1438234 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-f51974491b7143a887620a5f751af46f
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

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