Triethylamine → 3-Chloromethyl-4,4'-dimethylbiphenyl

HRID 22264Notes

Reaction equation

HRID 22264 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:8]=1[CH3:9].C(N(CC)CC)C.CS([Cl:28])(=O)=O>C(Cl)Cl>[Cl:28][CH2:2][C:3]1[CH:4]=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 183888713-Hydroxymethyl-4,4'-dimethylbiphenyl

Product 1

HCID 194303213-Chloromethyl-4,4'-dimethylbiphenyl

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-hydroxymethyl-4,4'-dimethylbiphenyl (1.3 g) and triethylamine (0.8 g) in methylene chloride (50 ml) was cooled to 0° C., and methanesulfonyl chloride (0.84 g) in methylene chloride was added dropwise. The mixture was allowed to warm to room temperature, and was stirred overnight. Ice/water was then added, the organic layer separated, the aqueous layer washed with methylene chloride, the organic layer washed with brine, dried over sodium sulfate, and the solvent evaporated under reduced pressure, to yield 3-chloromethyl-4,4'-dimethylbiphenyl as an oil.

Workup

  1. customthe organic layer separated
  2. washthe aqueous layer washed with methylene chloride
  3. washthe organic layer washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-95032b6d59a8442184d8e1698eefea94
Source dataset
uspto-grants-1995_06
Patent number
US05428037

Reaction notes

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