Acetonitrile → (4-Bromo-2-chloro-phenyl)-(2-fluoro-5-hydroxy-phenyl)-methanone
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[C:14]([O:16][Si](C(C)(C)C)(C)C)[CH:13]=[CH:12][C:11]=2[F:24])[OH:9])=[C:4]([Cl:25])[CH:3]=1.C(#N)C.C[N+]1([O-])CCOCC1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:11]=2[F:24])=[O:9])=[C:4]([Cl:25])[CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Compound 510 (15.9 g, 35.6 mmol) was dissolved in dry DCM (80 mL) and dry acetonitrile (10 mL) under an argon atmosphere. The mixture was cooled to 0° C. and added 4-methyl-morpholine 4-oxide (6.27 g, 53.5 mmol), grinded molecular sieve (4 Å, 17.8 g). Tetra-N-propylammonium perruthenate (VII) (250 mg, 0.71 mmol) was added in 5 portions (5×50 mg) and the reaction mixture was stirred for 10 min. at 0° C., evaporated to ⅓ volume and filtered through silica. The silica was washed with EtOAc (300 mL). The organic phase was concentrated in vacuo affording the crude product. Purified by continuously gradient flash chromatography using EtOAc/petroleum ether (40-60)(v:v=1:80 to 1:10) as the eluent, affording the title compound as a yellow solid.
Workup
- customgrinded molecular sieve (4 Å, 17.8 g)
- customevaporated
- filtrationfiltered through silica
- washThe silica was washed with EtOAc (300 mL)
- concentrationThe organic phase was concentrated in vacuo
- customaffording the crude product
- customPurified by continuously gradient flash chromatography
Sources & evidence
- ORD record
- ord-18ace6b616174ab490382786a796dde7
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977387B2
Reaction notes
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