3-(Chloromethyl)-2-methyl-1,1'-biphenyl → HCID 12256238, compound

HRID 1388941Notes

Reaction equation

HRID 1388941 reaction equation
Cl[CH2:2][C:3]1[C:4]([CH3:15])=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[I-].[CH3:17][N+:18](C)(C)[CH2:19]C1C(C2C=CC=CC=2)=CC=CC=1>>[CH3:17][N:18]([CH2:2][C:3]1[C:4]([CH3:15])=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1)[CH3:19]

Participants

3

Reactant 2

HCID 132825193-(Chloromethyl)-2-methyl-1,1'-biphenylHCID 13374112([1,1'-Biphenyl]-2-yl)-N,N,N-trimethylmethanaminium iodide

Product 1

HCID 12256238HCID 12256238, compound

Procedure

An additional method for preparing the intermediate 3-chloromethyl-2-methyl[1,1'-biphenyl] involves a Sommelet-Hauser rearrangement of N,N,N-trimethyl[1,1'-biphenyl]-2-methanaminium iodide to give 3-dimethylaminomethyl-2-methyl-[1,1'-biphenyl], which is then converted into the 3-chloromethyl derivative by treatment with ethyl chloroformate. The N,N,N-trimethyl-[1,1'-biphenyl]-2-methanaminium iodide starting material may be prepared in four steps from 2-biphenylcarboxylic acid via the acid chloride, dimethyl carboxamide, and dimethylaminomethyl derivatives.

Sources & evidence

ORD record
ord-040befc0c99c43a1a892261cec01a560
Source dataset
uspto-grants-1984_02
Patent number
US04434182

Reaction notes

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