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

HRID 2380208Notes

Reaction equation

HRID 2380208 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

6

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 11000144Benzene, 1-bromo-2-(methylthio)-4-(trifluoromethyl)-HCID 178418339Butyllithium

Product 1

HCID 11085762Benzoic acid, 2-(methylthio)-4-(trifluoromethyl)-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

n-Butyllithium (2.5M in hexane, 25 ml) was added under an inert atmosphere to a stirred solution of 4-bromo-3-(methylsulphenyl)benzotrifluoride (16.4 g) in ether maintaining the temperature below -70° C. for 2 hours. The mixture was poured onto solid carbon dioxide pellets, stirred for 10 mins and aqueous hydrochloric acid added. The layers were separated and the aqueous layer was extracted with ether. The combined organic layers were washed with water, dried (MgSO4) 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 (bs,1H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ether
  3. washThe combined organic layers were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated
  7. customthe residue was triturated with cyclohexane
  8. filtrationfiltered

Sources & evidence

ORD record
ord-2a499f8b88ea4ea189c444fd84e51c09
Source dataset
uspto-grants-1994_11
Patent number
US05366957

Reaction notes

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