Dimethylformamide → 1-(Chloromethyl)-4-fluoro-2-methylbenzene

HRID 1164352Notes

Reaction equation

HRID 1164352 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12]O)=[C:8]([CH3:14])[CH:7]=1.CN(C)C=O>CC1C=CC=CC=1>[Cl:3][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([F:5])=[CH:7][C:8]=1[CH3:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 3872017(4-Fluoro-2-methylphenyl)methanol

Product 1

HCID 205118161-(Chloromethyl)-4-fluoro-2-methylbenzeneYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To 14.3 parts of thionyl chloride is added dropwise a solution of 14 parts of 4-fluoro-2-methylbenzenemethanol and 0.9 parts of N,N-dimethylformamide in 45 parts of methylbenzene while cooling in ice-water. Then there are added 135 parts of methylbenzene and stirring is continued for 1 hour at room temperature. The reaction mixture is evaporated, yielding 17 parts (100%) of 1-(chloromethyl)-4-fluoro-2-methylbenzene as a residue.

Workup

  1. customThe reaction mixture is evaporated

Sources & evidence

ORD record
ord-d91ea89eefb84bd78f5f2ceb30f9874d
Source dataset
uspto-grants-1983_01
Patent number
US04369184

Reaction notes

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