Thionyl Chloride → 3-(4-Bromophenyl)propanoyl chloride

HRID 931512Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.S(Cl)([Cl:15])=O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([Cl:15])=[O:12])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 27356093-(4-Bromophenyl)propionic acid

Product 1

HCID 224116513-(4-Bromophenyl)propanoyl chlorideYield 99%

Procedure

A solution of 3-(4-bromophenyl)propanoic acid (14.5 g, 63.60 mmol, 1.00 equiv) in thionyl chloride (80 mL) was refluxed for 2 h. The reaction mixture was cooled to room temperature and then concentrated under vacuum to give 15.5 g (99%) of 3-(4-bromophenyl)propanoyl chloride as a light yellow oil.

Workup

concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-8b8fbb5e33db44c8b1d88be70659b201
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296732B2

Reaction notes

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