Benzoic Acid → 4-Chlorobenzoic Acid

HRID 1058126Notes

Reaction equation

HRID 1058126 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC=CC=1C(O)=O.BrC1C=CC=CC=1C.C([Li])CCC.C(=O)=O.[Cl:36]C1C=CC(Br)=CC=1>>[Cl:36][C:5]1[CH:6]=[CH:7][C:2]([C:1]([OH:9])=[O:8])=[CH:3][CH:4]=1

Participants

7

Reactant 6

HCID 243Benzoic AcidHCID 280Carbon Dioxide2×HCID 72362-BromotolueneHCID 7806p-BromochlorobenzeneHCID 83732-Methylbenzoic acidHCID 178418339Butyllithium2×

Product 1

HCID 63184-Chlorobenzoic AcidYield 90%

Procedure

Gilman et al., J. Am. Chem. Soc. 1940, 62, 2327f. describes the synthesis of benzoic acid derivatives by lithiation of the corresponding aryl bromides and subsequent carboxylation. The preparation of 2-methylbenzoic acid by reaction of o-bromotoluene with n-butyllithium and subsequent carboxylation with solid CO2 achieves a yield of 83.8%. The reaction of 4-chlorobromobenzene with n-butyllithium and CO2 gives 4-chlorobenzoic acid with a 90% yield.

Sources & evidence

ORD record
ord-02d3365e71b440e59c16f32251bdd0f1
Source dataset
uspto-grants-2003_02
Patent number
US06515143B2

Reaction notes

Loading…