Acetonitrile → [3-(2-Formyl-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid

HRID 885243Notes

Reaction equation

HRID 885243 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.F[C:13]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:14]=1[CH:15]=[O:16].C(=O)([O-])[O-].[K+].[K+].CC#N>C1COCC1>[CH:15]([C:14]1[CH:17]=[C:18]([C:21]([F:22])([F:23])[F:24])[CH:19]=[CH:20][C:13]=1[O:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1)=[O:16]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 121223'-Hydroxyphenylacetic acidHCID 27349042-Fluoro-5-(trifluoromethyl)benzaldehyde

Product 1

HCID 58237662[3-(2-Formyl-4-trifluoromethyl-phenoxy)-phenyl]-acetic acidYield 14.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Hydroxyphenylacetic acid (1.0 g, 5.2 mmol), 2-fluoro-5-(trifluoromethyl)benzaldehyde (1.0 g, 6.6 mmol), and potassium carbonate (2.2 g, 15.6 mmol) were combined in THF (20 mL) and MeCN (20 mL) and heated to 70° C. for 3 days. After acidic work-up, the crude material was purified by silica gel chromatography (20-100% EtOAc in hexanes) to give the desired product (0.25 g).

Workup

  1. customAfter acidic work-up, the crude material was purified by silica gel chromatography (20-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b123fe851e30466e9c1ef4f2111e5571
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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