Trifluoroacetic acid → (E)-4-(4-bromo-2,6-dimethylphenyl)but-2-enoic acid

HRID 735635Notes

Reaction equation

HRID 735635 reaction equation
C(O)(C(F)(F)F)=O.[Br:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH2:16]/[CH:17]=[CH:18]/[C:19]([O:21]C(C)(C)C)=[O:20])=[C:11]([CH3:26])[CH:10]=1>C(Cl)Cl>[Br:8][C:9]1[CH:10]=[C:11]([CH3:26])[C:12]([CH2:16]/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20])=[C:13]([CH3:15])[CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57842697(E)-tert-butyl 4-(4-bromo-2,6-dimethylphenyl)but-2-enoate

Product 1

HCID 57842884(E)-4-(4-bromo-2,6-dimethylphenyl)but-2-enoic acidYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (10 mL) was added to a solution of 53B (2.35 g) in CH2Cl2 (20 mL) at 0° C. and stirred for 4 h. The reaction mixture was concentrated to yield 53C (1.95 g, 99%) as an off-white solid. MS (ESI) m/z 267.2/269.2 (M−H)−.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-7c342f08004640c786b4b2607ba7c13e
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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