Methyl 4-benzyloxycarbonyl-2-fluorobenzoate → 1-Methyl 2-fluoro-1,4-benzenedicarboxylate
Reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:19]=[CH:18][C:7]([C:8]([O:10]CC2C=CC=CC=2)=[O:9])=[CH:6][C:5]=1[F:20]>CCO.CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:19]=[CH:18][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[F:20]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of the crude 2-fluoroterephthalic acid 4-benzyl ester 1-methyl ester (8, 0.14 mol) in EtOH (210 mL) and EtOAc (210 mL) is treated with 10% Pd/C (4.0 g) under hydrogen atmosphere at room temperature for 5 h. After filtration of the catalyst, the filtrate is evaporated in vacuo. Crystals are collected and washed with ether/hexane (1:1) to give 2-fluoroterephthalic acid 1-methyl ester (9) as white solid.
Workup
- filtrationAfter filtration of the catalyst
- customthe filtrate is evaporated in vacuo
- customCrystals are collected
- washwashed with ether/hexane (1:1)
Sources & evidence
- ORD record
- ord-172ff2449a4f4dbf9798c254e00dd233
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709470B2
Reaction notes
Loading…