Acetyl chloride → Acetic acid 2,6-difluorobenzyl ester

HRID 243248

Reaction equation

HRID 243248 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[F:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:7]=1[CH2:8][OH:9].C(N(CC)CC)C>C(Cl)Cl.O>[F:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:7]=1[CH2:8][O:9][C:1](=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 879212,6-Difluorobenzyl alcohol

Product 1

HCID 12084134Acetic acid 2,6-difluorobenzyl esterYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Acetyl chloride (1.13 mL, 15.8 mmol) was added dropwise to a solution of 2,6-difluorobenzyl alcohol (1.76 g, 12.2 mmol) and triethylamine (3.43 mL, 24.4 mmol) in DCM (20 mL) at 0° C. The reaction mixture was stirred at 0° C. for 30 min. The reaction mixture was diluted with water and extracted with DCM (3×20 mL). The combined organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, eluting with 0-100% EtOAc in cyclohexane) to yield the title compound as a colourless oil (1.72 g, 76%). 1H NMR 400 MHz δ (CDCl3): 7.37-7.28 (1H, m), 6.96-6.88 (2H, m), 5.20 (2H, s), 2.08 (3H, s).

Workup

  1. extractionextracted with DCM (3×20 mL)
  2. washThe combined organic fractions were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. washThe resultant residue was subjected to flash chromatography (SiO2, eluting with 0-100% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-1d6104a333ff4c25aed6fda04fe7a4c2
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Linked notes

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