Cornforth reagent → 1-(5-Bromo-2-fluorophenyl)ethanone
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH2:8][OH:9])[CH:7]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=C[CH:21]=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([C:8](=[O:9])[CH3:21])[CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
5-Bromo-2-fluoro-phenyl-methanol (50.0 g, 228 mmol) along with 300 mL DCM was charged into 2 liter round bottom flask. Crushed pyridinium dichromate (171.0 g, 456 mmol) and powdered molecular sieves (10 g) were both added into the flask. The heterogeneous reaction mixture was stirred for 16 hours at 20° C. The resulting reaction mixture was filtered through Celite and washed with ether (500 mL×3). The combined filtrate was concentrated under reduced pressure. The crude product was eluted through a short silica gel pad (3 inch in length) with 10% EtOAc in hexane. The resulting product (42.0 g, yield=84%) was used in the following step.
Workup
- additionboth added into the flask
- customThe resulting reaction mixture
- filtrationwas filtered through Celite
- washwashed with ether (500 mL×3)
- concentrationThe combined filtrate was concentrated under reduced pressure
- washThe crude product was eluted through a short silica gel pad (3 inch in length) with 10% EtOAc in hexane
Sources & evidence
- ORD record
- ord-a96fe9c82b3142029f3493dbf7d1189c
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07897619B2
Reaction notes
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