Thionyl Chloride → 6-Bromo-2-naphthoyl chloride

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=O)[CH:6]=[CH:5]2.S(Cl)([Cl:17])=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([Cl:17])=[O:14])[CH:6]=[CH:5]2

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 45498526-Bromo-2-naphthalenecarboxylic acid

Product 1

HCID 218796066-Bromo-2-naphthoyl chloride

Conditions

Temperature: 60 °C

Procedure

6-Bromonaphthalene-2-carboxylic acid (25.1 g) was suspended in thionyl chloride (200 mL), stirred at 60° C. for 16 hours and evaporated under vacuum. Solid was dissolved in dichloromethane (50 mL) and evaporated under vacuum, giving 6-bromonaphthalene-2-carbonyl chloride (27.0 g, crude) as a white solid.

Workup

customevaporated under vacuum
dissolutionSolid was dissolved in dichloromethane (50 mL)
customevaporated under vacuum

Sources & evidence

ORD record: ord-73404d95d15c4e4bb1380de649e4b62e
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822430B2

Reaction notes

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