Thionyl Chloride → 2-Chloro-6-fluoro-alpha-methylbenzyl chloride

HRID 1903835Notes

Reaction equation

HRID 1903835 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[CH:4](O)[CH3:5].S(Cl)([Cl:14])=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[CH:4]([Cl:14])[CH3:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 133042791-(2-Chloro-6-fluorophenyl)ethan-1-ol2×

Product 1

HCID 133042802-Chloro-6-fluoro-alpha-methylbenzyl chlorideYield 92.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-chloro-6-fluoro-alpha-methylbenzyl alcohol of (B) (45.1 g, 0.26 mol) is dissolved in chloroform (70 ml), and thionyl chloride (61.5 g, 0.52 mol) is added over a period of 30 minutes. The resultant mixture is refluxed for 16 hours. Excess thionyl chloroform are then removed on a rotary evaporator, resulting in pure title product (46.2 g, 92.6%).

Workup

  1. customExcess thionyl chloroform are then removed on a rotary evaporator

Sources & evidence

ORD record
ord-9ba5eb5e56164fd0b121fc1ed44dfc6d
Source dataset
uspto-grants-1984_03
Patent number
US04438271

Reaction notes

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