Thionyl Chloride → 3-Bromo-4-(2'-methylbutyl)benzoic acid chloride

Reaction equation

S(Cl)([Cl:3])=O.[Br:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH2:15][CH:16]([CH3:19])[CH2:17][CH3:18])[C:9](O)=[O:10]>>[Br:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH2:15][CH:16]([CH3:19])[CH2:17][CH3:18])[C:9]([Cl:3])=[O:10]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 198599663-Bromo-4-(2'-methylbutyl)benzoic acid

Product 1

HCID 538429803-Bromo-4-(2'-methylbutyl)benzoic acid chlorideYield 98.1%

Procedure

Thionyl chloride (118 g) was added to the 3-bromo-4-(2'-methylbutyl)benzoic acid (100 g, 0.37 mol) followed by refluxing the mixture for 2 hours and distilling off excess thionyl chloride under reduced pressure to obtain 3-bromo-4-(2'-methylbutyl)benzoic acid chloride (105.1 g).

Workup

temperatureby refluxing the mixture for 2 hours
distillationdistilling off excess thionyl chloride under reduced pressure

Sources & evidence

ORD record: ord-7960b18b5e314dc7a1ced42d775b266e
Source dataset: uspto-grants-1990_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04913838

Reaction notes

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