Carbon tetrabromide → 3,5-Difluoro-4-triisopropylsilanyloxybenzyl bromide

HRID 1921875ノート

反応式

HRID 1921875 の反応式
[F:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[CH:5]=[C:4]([F:10])[C:3]=1[O:11][Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14].[Br:22]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:22][CH2:8][C:6]1[CH:5]=[C:4]([F:10])[C:3]([O:11][Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])=[C:2]([F:1])[CH:7]=1

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 579718961,3-Difluoro-5-hydroxymethyl-2-triisopropylsilanyloxybenzene

生成物 1

HCID 579719463,5-Difluoro-4-triisopropylsilanyloxybenzyl bromide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

7.40 g (23.4 mmol) of 1,3-difluoro-5-hydroxymethyl-2-triisopropylsilanyloxybenzene are dissolved in 90 ml of dry dichloromethane by stirring at 0° C. under argon. 10.1 g (30.4 mmol) of tetrabromomethane and 7.97 g (30.4 mmol) of triphenylphosphine are successively added to this solution, and the mixture is then stirred under reflux under argon for 12 h. The reaction mixture is washed with water, the organic phase is separated off, dried over magnesium sulfate and filtered, and the solvent is distilled out in vacuo. The oily residue is taken up in diethyl ether and stirred at RT, then filtered, and the filtrate is concentrated. Chromatography of the residue on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 9:1) results in 7.42 g (15.6 mmol, 84% of theory) of the title compound.

後処理

  1. stirringthe mixture is then stirred
  2. temperatureunder reflux under argon for 12 h
  3. washThe reaction mixture is washed with water
  4. customthe organic phase is separated off
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. distillationthe solvent is distilled out in vacuo
  8. stirringstirred at RT
  9. filtrationfiltered
  10. concentrationthe filtrate is concentrated

出典と根拠

ORDレコード
ord-2aa110eae3014579aa1cd98e37f48bf7
出典データセット
uspto-grants-2012_05
特許番号
US08173704B2

反応ノート

読み込み中…