2-Fluoro-4-nitrotoluene → 2-Fluoro-4-nitrobenzoic acid

HRID 484056Notes

Reaction equation

HRID 484056 reaction equation
[F:1][C:2]1[CH:17]=[C:16](O)[CH:15]=[CH:14][C:3]=1[C:4]([O:6]CC1C=CC=CC=1)=[O:5].FC1C=C([N+:26]([O-:28])=[O:27])C=CC=1C.[O-][Mn](=O)(=O)=O.[K+]>>[F:1][C:2]1[CH:17]=[C:16]([N+:26]([O-:28])=[O:27])[CH:15]=[CH:14][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 740252-Fluoro-4-nitrotolueneHCID 516875Potassium PermanganateHCID 18006244Benzyl 2-fluoro-4-hydroxybenzoate

Product 1

HCID 3026792-Fluoro-4-nitrobenzoic acid

Procedure

This was prepared as described above in Example 33 except that benzyl 2-fluoro-4-hydroxybenzoate (prepared from 2-fluoro-4-nitrotoluene by oxidation with KMnO4 to give 2-fluoro-4-nitrobenzoic acid, followed by catalytic reduction to give 4-amino-2-fluorobenzoic acid, followed by diazotization/hydrolysis to give 4-hydroxy-2-fluorobenzoic acid which was converted to benzyl 2-fluoro-4-hydroxybenzoate in a fashion analogous to that described in Example 23) was used as starting material in place of benzyl 2-chloro-4-hydroxybenzoate.

Workup

  1. customThis was prepared

Sources & evidence

ORD record
ord-288cd257beaf412d9fc874a8c02af4b3
Source dataset
uspto-grants-1993_07
Patent number
US05229381

Reaction notes

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