p-Bromochlorobenzene → HCID 11461534, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.[Li]CCCC.CN(CCN(C)C)C.[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([CH:35]=[O:36])[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]>C1COCC1>[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([CH:35]([C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=2)[OH:36])[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]Participants
6
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 4-bromochlorobenzene (1.35 g, 7.03 mmol) in THF (30 mL) cooled to −78° C. was added n-BuLi (2.5M in THF, 3.00 mL, 7.5 mmol) and the mixture was stirred at −78° C. for 30 minutes. TMEDA (1.06 mL, 7.02 mmol) and 4-formyl-piperidine-1-carboxylic acid tert-butyl ester (1.00 g, 4.69 mmol) in THF (10 mL) were added and the mixture stirred at −78° C. for 3 hours. The reaction was quenched with saturated aqueous NH4Cl (30 mL) and after work-up and purification afforded 4-[(4-chloro-phenyl)-hydroxy-methyl]-piperidine-1-carboxylic acid tert-butyl ester as a white solid (450 mg, 30%).
Workup
- stirringthe mixture stirred at −78° C. for 3 hours
- customThe reaction was quenched with saturated aqueous NH4Cl (30 mL)
- customafter work-up and purification
Sources & evidence
- ORD record
- ord-2b674c238e41467bb8b71083b858bf06
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07491735B2
Reaction notes
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