Triphenylphosphine → Methyl 5-fluoro-2-[2-(4-trifluoromethylphenyl)ethoxy]benzoate

HRID 1672653Notes

Reaction equation

HRID 1672653 reaction equation
[F:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]([OH:12])=[CH:4][CH:3]=1.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22]O)=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:22][CH2:21][C:18]2[CH:17]=[CH:16][C:15]([C:14]([F:13])([F:24])[F:25])=[CH:20][CH:19]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2783186Methyl 5-fluoro-2-hydroxybenzoateHCID 112755102-(4-(Trifluoromethyl)phenyl)ethan-1-ol

Product 1

HCID 57864408Methyl 5-fluoro-2-[2-(4-trifluoromethylphenyl)ethoxy]benzoateYield 58.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.79 g (10.5 mmol) of methyl 5-fluorosalicylate, 20 g (10.5 mmol) of 2-(4-trifluoromethylphenyl)ethanol and 2.76 g (10.5 mmol) of triphenylphosphine are introduced into 50 ml of THF and, at 0° C., a solution of 1.83 g (10.5 mmol) of diethyl azodicarboxylate in 10 ml of THF is added dropwise. The mixture is stirred at RT overnight and then the volatile components are removed in vacuo. The resulting crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:1). 2.09 g (58% yield) of the title compound are obtained.

Workup

  1. customthe volatile components are removed in vacuo
  2. customThe resulting crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:1)

Sources & evidence

ORD record
ord-d35df0c05b3447aca7a798121bea81a8
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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