Ethyl chloroformate → 3-(Chloromethyl)-2-methyl-1,1'-biphenyl

HRID 2418801Notes

Reaction equation

HRID 2418801 reaction equation
CN(C)[CH2:3][C:4]1[C:5]([CH3:16])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1.[Cl:18]C(OCC)=O>C1(C)C=CC=CC=1>[Cl:18][CH2:3][C:4]1[C:5]([CH3:16])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 12256238HCID 12256238, compound

Product 1

HCID 132825193-(Chloromethyl)-2-methyl-1,1'-biphenylYield 104.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

Under a dry nitrogen atmosphere, 0.5 g (0.0022 mole) of N,N,2-trimethyl-[1,1'-biphenyl]-3-methanamine was dissolved in 5.5 ml of dry toluene with stirring and the solution was heated to 80° C. A solution of 0.36 g (0.0033 mole) of ethyl chloroformate in 1.1 ml of dry toluene was added dropwise during 5 minutes. The reaction mixture was stirred for 3.3 hours at 80° C., then cooled to room temperature and filtered. The solvent was removed from the filtrate under reduced pressure to give 0.5 g (100% yield) of 3-chloromethyl-2-methyl-[1,1'-biphenyl] as a light orange oil.

Workup

  1. stirringThe reaction mixture was stirred for 3.3 hours at 80° C.
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. customThe solvent was removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-19a868d8a9934b019bcdd07e05afe078
Source dataset
uspto-grants-1984_09
Patent number
US04473709

Reaction notes

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