Boron tribromide → 9a-butyl-8-chloro-6-fluoro-7-hydroxy-4-(trifluoromethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7900ノート

反応式

HRID 7900 の反応式
[CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[C:14]([C:19]([F:22])([F:21])[F:20])=[C:13]1[C:12]1[C:7](=[C:8]([Cl:26])[C:9]([O:24]C)=[C:10]([F:23])[CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].B(Br)(Br)Br>ClCCl>[CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[C:14]([C:19]([F:21])([F:20])[F:22])=[C:13]1[C:12]1[C:7](=[C:8]([Cl:26])[C:9]([OH:24])=[C:10]([F:23])[CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 219909349a-butyl-8-chloro-6-fluoro-7-methoxy-4-(trifluoromethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one

生成物 1

HCID 99698059a-butyl-8-chloro-6-fluoro-7-hydroxy-4-(trifluoromethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 9a-butyl-8-chloro-6-fluoro-7-methoxy-4-(trifluoromethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one (39 mg, 0.10 mmol) in anhydrous dichloromethane (1.0 mL) was cooled in a dry ice-acetone bath (−78° C.) and the solution was treated with 1M boron tribromide in dichloromethane (0.3 mL, 0.3 mmol). The cooling bath was removed and the mixture was stirred at room temperature for one hour. The mixture was partitioned between EtOAc (20 mL) and water (20 mL) containing 2N HCl (1 mL). The organic phase was washed with brine (10 mL), dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate, developing with 10% EtOAc in CH2Cl2. The product band was eluted with 10% MeOH in CH2Cl2, the eluent evaporated under vacuum, and the residue lyophilized from benzene plus a few drops of EtOH to afford 9a-butyl-8-chloro-6-fluoro-7-hydroxy-4-(trifluoromethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an amorphous solid.

後処理

  1. customThe cooling bath was removed
  2. customThe mixture was partitioned between EtOAc (20 mL) and water (20 mL)
  3. additioncontaining 2N HCl (1 mL)
  4. washThe organic phase was washed with brine (10 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. customThe residue was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate
  9. washThe product band was eluted with 10% MeOH in CH2Cl2
  10. customthe eluent evaporated under vacuum

出典と根拠

ORDレコード
ord-2114ab91aa8947dd91beb80fa17fd697
出典データセット
uspto-grants-2006_08
特許番号
US07087599B2

反応ノート

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