Thionyl Chloride → 3-Nitro-5-(trifluoromethyl)benzoyl chloride

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7](O)=[O:8])([O-:3])=[O:2].S(Cl)([Cl:19])=O>>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7]([Cl:19])=[O:8])([O-:3])=[O:2]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 6166023-Nitro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 226083993-Nitro-5-(trifluoromethyl)benzoyl chloride

Procedure

A solution of thionyl chloride (30 ml) and 3-nitro-5-(trifluoromethyl)benzoic acid (10 g) was heated to reflux for 2 h. The reaction mixture was concentrated under reduced pressure and azeotroped with toluene (10 ml—removed under reduced pressure) to afford 3-nitro-5-(trifluoromethyl)benzoyl chloride.

Workup

temperatureto reflux for 2 h
concentrationThe reaction mixture was concentrated under reduced pressure
customazeotroped with toluene (10 ml—removed under reduced pressure)

Sources & evidence

ORD record: ord-8c96f968b55f49029bd9be4cd9d70eef
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557996B2

Reaction notes

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