Thionyl Chloride → 8-bromooctanoyl Chloride

HRID 327357Notes

Reaction equation

[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O.S(Cl)([Cl:14])=O>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([Cl:14])=[O:11]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 5482758-Bromooctanoic acid

Product 1

HCID 114022288-bromooctanoyl Chloride

Procedure

8-Bromooctanoic acid (200 g) was added slowly to thionyl chloride (325 ml). The mixture was stirred at 60° for 1 hour. Excess thionyl chloride distilled off in vacuo. The dark oily residue was distilled to give 8-bromooctanoyl chloride as colorless oil, b.p. 112°-114°/0.1-0.3 mm Hg, (202.38, 93%).

Workup

distillationExcess thionyl chloride distilled off in vacuo
distillationThe dark oily residue was distilled

Sources & evidence

ORD record: ord-c2c46ba0ffbf4f4dafe406546b36d248
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05273740

Reaction notes

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