Imidazole → Methyl 4-(4-fluorophenyl)-4-iodobutanoate
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.[F:27][C:28]1[CH:33]=[CH:32][C:31]([CH:34](O)[CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[CH:30][CH:29]=1>C(Cl)Cl>[F:27][C:28]1[CH:33]=[CH:32][C:31]([CH:34]([I:25])[CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[CH:30][CH:29]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of triphenylphosphine (419 mg, 1.6 mmol) in anhydrous 20 mL DCM was added imidazole (224 mg, 3.3 mmol) and iodine (406 mg, 1.6 mmol) at 0° C. The reaction mixture was stirred for 30 min at 0° C. and then methyl 4-(4-fluorophenyl)-4-hydroxybutanoate (212 mg, 1 mmol) in 10 mL DCM was added to the mixture. The resulting mixture was stirred at 0° C. for 2 h and the temperature was slowly raised to room temp over a period of 3 h. Evaporation of solvent left the crude product as an oil from which the product was isolated by Flash column chromatography eluting with 0% to 10% ethyl acetate/hexane to give the title compound, 161 mg, as a light yellow oil.
Workup
- stirringThe resulting mixture was stirred at 0° C. for 2 h
- temperaturethe temperature was slowly raised to room temp over a period of 3 h
- customEvaporation of solvent
- waitleft the crude product as an oil from which the product
- customwas isolated by Flash column chromatography
- washeluting with 0% to 10% ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-f370be41c08e45109bae58e79ae32147
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119692B2
Reaction notes
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