Tributylstannane → 2,4,5-Trifluoro-3-methylbenzoic acid

HRID 1721099Notes

Reaction equation

HRID 1721099 reaction equation
[F:1][C:2]1[C:11]([CH2:12][N+]([O-])=O)=[C:10]([F:16])[C:9]([F:17])=[C:4](C(OC)=O)[C:3]=1[C:18]([O:20]C)=[O:19].C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N>C1C=CC=CC=1>[F:1][C:2]1[C:11]([CH3:12])=[C:10]([F:16])[C:9]([F:17])=[CH:4][C:3]=1[C:18]([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 22417098HCID 22417098, compound

Product 1

HCID 118055142,4,5-Trifluoro-3-methylbenzoic acidYield 86.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4.6 g of compound 42, 6.8 g of tributyltin hydride, 300 mg of α,α'-azobisisobutyronitrile and 70 ml of benzene was refluxed for 4 hours. The reaction mixture was then concentrated under reduced pressure and the residue was subjected to silica gel (50 g) column chromatography eluting with benzene. The procedure gave 2.45 g of title compound 45as a light yellow coil.

Workup

  1. temperaturewas refluxed for 4 hours
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. washeluting with benzene

Sources & evidence

ORD record
ord-85dadbfaecb0466fb5cc7f7b2782140e
Source dataset
uspto-grants-1996_04
Patent number
US05508428

Reaction notes

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