Acetyl chloride → Acetic acid, (2-fluoro-5-nitrophenyl)methyl ester

HRID 1593061Notes

Reaction equation

HRID 1593061 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH2:4][OH:5].C(N(CC)CC)C.[C:20](Cl)(=[O:22])[CH3:21]>ClCCl.C(OCC)(=O)C>[F:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH2:4][O:5][C:20](=[O:22])[CH3:21]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 4437169(2-Fluoro-5-nitrophenyl)methanol

Product 1

HCID 58998466Acetic acid, (2-fluoro-5-nitrophenyl)methyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-fluoro-5-nitrobenzyl alcohol (1 g, 5.84 mmol) in 5 mL dichloromethane and triethylamine (0.81 ml, 5.84 mmol), was added acetyl chloride (0.415 ml, 1 eq) dropwise. The solution was stirred at room temperature for 12 hours, diluted with ethyl acetate and extracted with brine. Combine organic layers was dried over sodium sulfate, concentrated in vacuo to give acetic acid 2-fluoro-5-nitro-benzyl ester.

Workup

  1. extractionextracted with brine
  2. dry with materialCombine organic layers was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3073f91f13654132910e07b6f1ce6d29
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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