Dimethylformamide → 4-Fluorophenylacetyl chloride

HRID 51277

Reaction equation

HRID 51277 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.CN(C)C=O.C(Cl)(=O)C([Cl:20])=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([Cl:20])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 98372-(4-Fluorophenyl)acetic acidHCID 65578Oxalyl chloride

Product 1

HCID 37449884-Fluorophenylacetyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

Into a suitable agitated reactor is charged 4-fluorophenylacetic acid (79.4 kg, 515 mol), N,N-dimethylformamide (0.5 kg, 6.8 mol), and toluene (318 kg). Oxalyl chloride (68.3 kg, 538 mol) is added at a rate as to maintain the temperature below 35° C. The solution is stirred for at least 7 hours at about 25° C., typically affording a 22.1 wt % solution of 4-fluorophenylacetyl chloride.1

Workup

  1. temperatureto maintain the temperature below 35° C

Sources & evidence

ORD record
ord-8fc5d48602a040af9095623c7c408705
Source dataset
uspto-grants-2004_03
Patent number
US06713627B2

Linked notes

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