Carbon Dioxide → HCID 53695089, compound

HRID 2393040Notes

Reaction equation

HRID 2393040 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH2:14][CH3:15])=[CH:9][C:8]=1[C:16]([F:19])([F:18])[F:17].[C:20](=[O:22])=[O:21].Cl>CCCCCC.CCOCC>[CH2:14]([S:13][C:10]1[CH:11]=[CH:12][C:7]([C:20]([OH:22])=[O:21])=[C:8]([C:16]([F:19])([F:18])[F:17])[CH:9]=1)[CH3:15]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 54056709HCID 54056709, compoundHCID 178418339Butyllithium

Product 1

HCID 53695089HCID 53695089, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of n-butyllithium in hexane (2.5M, 115 ml) was added dropwise with cooling to a stirred solution of 2-bromo-5-(ethylsulphenyl)benzotrifluoride (80.0 g) in anhydrous ether whilst maintaining the temperature below -70° C. The mixture was stirred at -78° C. for 1.5 hours and poured onto solid carbon dioxide pellets. The mixture was stirred for 20 minutes then treated with hydrochloric acid (2M). The layers were separated and the organic layer was washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness. The residue was triturated with cyclohexane and filtered to give 4-(ethylsulphenyl)-2-trifluoromethylbenzoic acid as an off-white solid, m.p. 133.5° C.

Workup

  1. temperaturewhilst maintaining the temperature below -70° C
  2. stirringThe mixture was stirred for 20 minutes
  3. customThe layers were separated
  4. washthe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customThe residue was triturated with cyclohexane
  9. filtrationfiltered

Sources & evidence

ORD record
ord-375d573c46584ca1aa93754399956765
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

Loading…