Cornforth reagent → HCID 69204766, compound

HRID 2373820Notes

Reaction equation

HRID 2373820 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:2].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[F:22][C:23]1[C:24]([O:41][CH3:42])=[C:25]([CH:39]=[O:40])[CH:26]=[C:27]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=2)[CH:28]=1>O>[F:22][C:23]1[C:24]([O:41][CH3:42])=[C:25]([C:39]([OH:2])=[O:40])[CH:26]=[C:27]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=2)[CH:28]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagent2×HCID 86597147HCID 86597147, compound

Product 1

HCID 69204766HCID 69204766, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Pyridinium dichromate (0.25 g, 0.67 mmol ) was added to a solution of 5-Fluoro-4-methoxy-4′-trifluoromethyl-biphenyl-3-carbaldehyde (0.2 g, 0.67 mmol) DMF (2 mL) and stirred for 12 h, to complete the reaction more pyridinium dichromate (0.2 g , 0.53 mmol) was added and stirred for 12 h. The reaction mixture was diluted with water (5 mL) and extracted with EtOAc(10 mL). Solvent was removed under reduced pressure to get 5-Fluoro-4-methoxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid (0.12 g).

Workup

  1. additionwas added
  2. stirringstirred for 12 h
  3. extractionextracted with EtOAc(10 mL)
  4. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-97e33b695f154a3d811a0427d832f52c
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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