Benzoic Acid → Benzoyl fluoride

HRID 325165

Reaction equation

HRID 325165 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N(S(F)(F)[F:24])C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[C:1]([F:24])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 243Benzoic AcidHCID 9859911Diphenylaminosulfur trifluoride

Product 1

HCID 67999Benzoyl fluorideYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzoic acid (122 mg, 1 mmol) in CH2Cl2 (5.0 mL) was added to diphenylaminosulfur trifluoride (771 mg, 3.0 mmol ) under N2 and stirred for 16 h at room temperature. After work-up as above benzoyl fluoride (124 mg, quantitative yield) was obtained. The product was identified by g.c.m.s. M+=124

Sources & evidence

ORD record
ord-a908a86135bb47f298ee905e61b0d722
Source dataset
uspto-grants-2001_04
Patent number
US06222064B1

Linked notes

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