Benzene, 1-bromo-4-(trifluoromethyl)- → Methanone, (3-methoxyphenyl)[4-(trifluoromethyl)phenyl]-
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.C([Li])CCC.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([O-])=[O:23].[Na+]>CCOCC.O>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([C:22](=[O:23])[C:21]2[CH:25]=[CH:26][CH:27]=[C:19]([O:18][CH3:17])[CH:20]=2)=[CH:3][CH:4]=1Participants
Procedure
This is carried out under nitrogen at -60° C. 0.29 mol (65 g) of para-bromo-trifluoromethylbenzene dissolved in 100 ml of anhydrous ether is added dropwise to 0.29 mol of butyl-lithium in solution in ether (1.48 mol/liter). The reaction is followed by gas phase chromatography; when there is no longer any remaining para-bromo-trifluoromethylbenzene, 0.29 mol (50.5 g) of sodium 3-methoxybenzoate is added. The mixture is allowed to return to ambient temperature. After stirring for 64 hours, it is hydrolysed in iced water. The batch is extracted with ether. The ether phase is dried, decolorised and concentrated. 45 g of a product which has been recrystallised from a mixture of isopropyl ether and hexane are obtained. Melting point 69° C. Yield: 55%.
Workup
- customThis is carried out under nitrogen at -60° C
- additionis added
- customto return to ambient temperature
- extractionThe batch is extracted with ether
- dry with materialThe ether phase is dried
- concentrationconcentrated
- custom45 g of a product which has been recrystallised from a mixture of isopropyl ether and hexane
- customare obtained
Sources & evidence
- ORD record
- ord-30e8ff838aa7477eb0caa43c0c3e7ef1
- Source dataset
- uspto-grants-1981_09
- Patent number
- US04287209
Reaction notes
Loading…