Dimethyl Sulfoxide → 4-Bromo-2-(trifluoromethyl)benzoic acid

HRID 1695132Notes

Reaction equation

HRID 1695132 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1.[C-]#N.[K+].[OH2:16].[OH-:17].[Na+].[CH3:19]S(C)=O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:19]([OH:17])=[O:16])=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1

Participants

6

Reactant 5

HCID 679Dimethyl Sulfoxide2×HCID 962WaterHCID 9032Potassium CyanideHCID 14798Sodium HydroxideHCID 27363255-Bromo-2-fluorobenzotrifluoride

Product 1

HCID 250673924-Bromo-2-(trifluoromethyl)benzoic acid

Conditions

Temperature
80 °C

Procedure

A mixture of 1-bromo-4-fluoro-3-(trifluoromethyl)benzene (5.02 g) and potassium cyanide (1.38 g) in DMSO (20 ml) was heated at 80° C. for 14 h. Water was added and the mixture was extracted ether, the organic extracts were dried (MgSO4) and evaporated to give a brown oil. This was dissolved in DMSO (10 ml) and 4 M NaOH (10 ml) and heated at 100° C. for 16 h. 2 M Hcl (20 ml) was added and the mixture was extracted with DCM (three times), the organic extracts were dried (MgSO4), evaporated and purified by chromatography (silica, CH2Cl2-MeOH—AcOH as eluent) to give the sub-title compound (1.99 g).

Workup

  1. extractionthe mixture was extracted ether
  2. dry with materialthe organic extracts were dried (MgSO4)
  3. customevaporated
  4. customto give a brown oil
  5. addition2 M Hcl (20 ml) was added
  6. extractionthe mixture was extracted with DCM (three times)
  7. dry with materialthe organic extracts were dried (MgSO4)
  8. customevaporated
  9. custompurified by chromatography (silica, CH2Cl2-MeOH—AcOH as eluent)

Sources & evidence

ORD record
ord-a44b13f8ab9d4bc6b7d776038a84c03b
Source dataset
uspto-grants-2012_04
Patent number
US08163727B2

Reaction notes

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