Thionyl Chloride → 1-Bromo-2-(chloromethyl)-4-(trifluoromethyl)benzene

HRID 2387443Notes

Reaction equation

HRID 2387443 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[CH2:12]O.S(Cl)([Cl:16])=O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[CH2:12][Cl:16]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 27562482-Bromo-5-(trifluoromethyl)benzyl alcohol

Product 1

HCID 201915011-Bromo-2-(chloromethyl)-4-(trifluoromethyl)benzene

Procedure

To [2-bromo-5-(trifluoromethyl)phenyl]methanol (4.4 g, 17 mmol) was added thionyl chloride (5 mL) and the resulting mixture was stirred at room temperature for 1 h. Evaporation in vacuo gave the crude product as an oil. 1H NMR (CDCl3) δ 7.77 (d, J=8.3 Hz, 1H), 7.73 (d, J=2.0 Hz, 1H), 7.53 (dd, J=8.5, 2.2 Hz, 1H), 5.66 (d, J=12.7 Hz, 1H), 5.46 (d, J=12.2 Hz).

Workup

  1. customEvaporation in vacuo

Sources & evidence

ORD record
ord-7241f75264a344ff8fb426f482552ad5
Source dataset
uspto-grants-2012_09
Patent number
US08268826B2

Reaction notes

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