Thionyl Chloride → Benzeneacetyl chloride, 4-bromo-

HRID 1454424Notes

Reaction equation

O=S(Cl)[Cl:3].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=O)=[CH:8][CH:7]=1>>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([Cl:3])=[O:15])=[CH:8][CH:7]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 181552Benzeneacetyl chloride, 4-bromo-Yield 99.5%

Conditions

Temperature: 60 °C

Procedure

In a 1 L flask, topped with an HCl trap, SOCl2 (495 ml; 3 vols) was added into (4-bromo-phenyl)-acetic acid (IIa) (165 g; 767.28 mmol). The reaction mixture was stirred at 60° C. for 3 h. Then, it was concentrated under vacuum and co-evaporated with toluene (100 mL). The resulting light brown oil was dried under vacuum for 48 h protected from the light using an aluminum foil. The title compound (m=178.20 g) was obtained as oil in a yield of 99.5%.

Workup

customIn a 1 L flask, topped with an HCl trap
concentrationThen, it was concentrated under vacuum and co-evaporated with toluene (100 mL)
customThe resulting light brown oil was dried under vacuum for 48 h

Sources & evidence

ORD record: ord-2d82d3f2cc6f4fe9ba1468f532d679de
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07479575B2

Reaction notes

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