Carbon Dioxide → Benzoic acid, 3-fluoro-4-(methylthio)-2-(trifluoromethyl)-

HRID 1041839Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[C:4]([F:10])[C:3]=1[C:11]([F:14])([F:13])[F:12].C([Li])CCC.[C:20](=[O:22])=[O:21].[OH-].[Na+]>C(OCC)C.CCCCCC.O>[F:10][C:4]1[C:3]([C:11]([F:14])([F:13])[F:12])=[C:2]([CH:7]=[CH:6][C:5]=1[S:8][CH3:9])[C:20]([OH:22])=[O:21]

Participants

Conditions

Temperature: -78 °C

Procedure

21.0 g (72.98 mmol) of 1-bromo-3-fluoro-4-(methylsulfanyl)-2-(trifluoromethyl)benzene were dissolved in 275 ml of absolute diethyl ether and cooled to −78° C. 54.8 ml (87.59 mmol) of a 1.6M solution of n-butyllithium in hexane were slowly added dropwise, and the resulting solution was stirred at −78° C. for 60 minutes. The reaction mixture was then added to freshly ground dry ice and slowly warmed to RT. Water was added, and the reaction mixture was made alkaline using 2M NaOH solution and washed with diethyl ether. The aqueous phase was then acidified with 51M HCl solution, causing the product to precipitate. The precipitate was filtered off with suction and dried under reduced pressure.

Workup

temperatureslowly warmed to RT
washwashed with diethyl ether
customto precipitate
filtrationThe precipitate was filtered off with suction
customdried under reduced pressure

Sources & evidence

ORD record: ord-d69f75e395a643b09496865f19970753
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557741B2

Reaction notes

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