Thionyl Chloride → 4-Bromo-1-(1-chloro-4,4,4-trifluorobutyl)-2-methylbenzene

HRID 1520245Notes

Reaction equation

HRID 1520245 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[C:4]([CH3:16])[CH:3]=1.S(Cl)([Cl:19])=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([Cl:19])[CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[C:4]([CH3:16])[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1158086891-(4-Bromo-2-methylphenyl)-4,4,4-trifluorobutan-1-ol

Product 1

HCID 1178403124-Bromo-1-(1-chloro-4,4,4-trifluorobutyl)-2-methylbenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-(4-bromo-2-methylphenyl)-4,4,4-trifluorobutan-1-ol (545 g) in toluene (5.4 L) was added thionyl chloride (393 g) at room temperature. The reaction mixture was stirred at 50° C. overnight and concentrated under reduced pressure to give the title compound. This reaction was performed for 3 batches, and the obtained compounds were used in step D without further purification.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6c5e7ccdc5094440a688dcc4a95ac16d
Source dataset
uspto-grants-2015_07
Patent number
US09073864B2

Reaction notes

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