Trifluoroacetic acid → 4-(4-Cyanophenyl)-3-methylbenzoic acid

HRID 392986Notes

Reaction equation

HRID 392986 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17]C(C)(C)C)=[O:16])=[CH:11][C:10]=2[CH3:22])=[CH:5][CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][C:10]=2[CH3:22])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22660788Tert-butyl 4'-cyano-2-methyl-1,1'-biphenyl-4-carboxylate

Product 1

HCID 226608164-(4-Cyanophenyl)-3-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Step 2) To a solution of the preceding ester (3.0 g, 10.2 mmol) in methylene chloride (75 mL) at 0° C. was added TFA (75 mL) dropwise over 10 min. The ice bath was removed and stirring continued for 1 h at rt. The mixture was concentrated on a rotary evaporator and then diluted with toluene and reconcentrated to afford 4′-cyano-2-methyl-1,1′-biphenyl-4-carboxylic acid. ESI-MS m/e 228.1 (M+1).

Workup

  1. customThe ice bath was removed
  2. concentrationThe mixture was concentrated on a rotary evaporator
  3. additiondiluted with toluene

Sources & evidence

ORD record
ord-894e81a012a841c3875a017c08803e03
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

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