Thionyl Chloride → 3-Benzyl-4-bromo-butyryl chloride

HRID 8219Notes

Reaction equation

[CH2:1]([CH:8]([CH2:13][Br:14])[CH2:9][C:10](O)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:17])=O>>[CH2:1]([CH:8]([CH2:13][Br:14])[CH2:9][C:10]([Cl:17])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 156918353-Benzyl-4-bromo-butyric acid

Product 1

HCID 219929293-Benzyl-4-bromo-butyryl chlorideYield 127%

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-benzyl-4-bromo-butyric acid (2.0 g, 7.78 mmol) and thionyl chloride (6.0 mmol) is heated to 80° C. for 2 h. The thionyl chloride is evaporated to yield 3-benzyl-4-bromo-butyryl chloride 2.1 g (99%), as a colorless liquid.

Workup

customThe thionyl chloride is evaporated

Sources & evidence

ORD record: ord-a73591ed459f4fe0b68338a627538e04
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087626B2

Reaction notes

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