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

HRID 1288740Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=1[S:17][CH3:18].[C:19](=[O:21])=[O:20].Cl>CCOCC>[CH3:18][S:17][C:8]1[CH:9]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:11]=[CH:12][C:7]=1[C:19]([OH:21])=[O:20]

Participants

Conditions

Temperature: -70 °C

Procedure

n-Butyllithium (2.5M solution in hexane; 25 ml) was added under an inert atmosphere to a stirred solution 4-bromo-3-methylsulphenylbenzotrifluoride (16.4 g) in ether whilst maintaining the temperature below -70° C. The mixture was stirred at -70° C. for 2 hours and then poured onto solid carbon dioxide pellets. The mixture was stirred for 10 minutes and aqueous hydrochloric acid was added. The layers were separated and the aqueous layer was extracted with ether. The combined organic layers were washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated and the residue was triturated with cyclohexane and filtered to give 2-methylsulphenyl-4-trifluoromethylbenzoic acid (12.4 g) as a white solid, NMR [CDCl3 +DMSO-d6 ]: 2.45 (s,3H), 7.2(d,1H), 7.3(s,1H), 8.0 (d,1H), 10.7-11.1 (bs,1H).

Workup

temperaturewhilst maintaining the temperature below -70° C
stirringThe mixture was stirred for 10 minutes
customThe layers were separated
extractionthe aqueous layer was extracted with ether
washThe combined organic layers were washed with water
dry with materialdried (anhydrous magnesium sulphate)
filtrationfiltered
customThe filtrate was evaporated
customthe residue was triturated with cyclohexane
filtrationfiltered

Sources & evidence

ORD record: ord-932d159eb5f84c64806fda2f43ea85d4
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05747424

Reaction notes

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