3-Chlorobenzaldehyde → (4-Bromo-3-thienyl)(3-chlorophenyl)methanol
Reaction equation
Br[C:2]1[C:6]([Br:7])=[CH:5][S:4][CH:3]=1.[Li]CCCC.[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=[O:18]>CCOCC>[Br:7][C:6]1[C:2]([CH:17]([C:16]2[CH:19]=[CH:20][CH:21]=[C:14]([Cl:13])[CH:15]=2)[OH:18])=[CH:3][S:4][CH:5]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
3,4-Dibromothiophene (15.5 g, 64.1 mmol) was added dropwise to a solution of n-BuLi (2.5M in hexane, 25.6 mL, 64.1 mmol) in Et2O (50 mL) at −78° C. After 1.5 h, 3-chlorobenzaldehyde (7.29 mL, 64.1 mmol) was added dropwise to the beige suspension. The resulting solution was stirred at −78° C. for 1 h and allowed to warm to 0° C. After 1 h, the reaction was quenched by the addition of 25% aq. NH4OAc. The aqueous layer was extracted with EtOAc and the combined organics were washed with water and brine, dried (Na2SO4) and concentrated to afford the desired product as a pale yellow oil. The crude product was used directly without further purification.
Workup
- temperatureto warm to 0° C
- waitAfter 1 h
- customthe reaction was quenched by the addition of 25% aq. NH4OAc
- extractionThe aqueous layer was extracted with EtOAc
- washthe combined organics were washed with water and brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3a9e2f4105894684849b66f8e2851b33
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969394B2
Reaction notes
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