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

HRID 1921862Notes

Reaction equation

HRID 1921862 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.CCOC(/N=N/C(OCC)=O)=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 2783186Methyl 5-fluoro-2-hydroxybenzoateHCID 5462977Diethyl azodicarboxylateHCID 112755102-(4-(Trifluoromethyl)phenyl)ethan-1-ol

Product 1

HCID 57864408Methyl 5-fluoro-2-[2-(4-trifluoromethylphenyl)ethoxy]benzoate

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-trifluoromethyl-phenyl)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 DEAD in 10 ml of THF is added dropwise. The mixture is stirred at RT overnight and the volatile components are then 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% of theory) of the title compound are obtained.

Workup

  1. customthe volatile components are then 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-f98faaab1e8d4bef9d97fc71cb2ed5cb
Source dataset
uspto-grants-2012_05
Patent number
US08173704B2

Reaction notes

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