1-Bromo-4-phenylmethoxybenzene → 4-n-Pentyl-4'-benzyloxybiphenyl

HRID 493038ノート

反応式

HRID 493038 の反応式
[Mg].[CH2:2]([C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1)[CH2:3][CH2:4][CH2:5][CH3:6].[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25](Br)=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1>[CH2:2]([C:7]1[CH:12]=[CH:11][C:10]([C:25]2[CH:26]=[CH:27][C:22]([O:21][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:23][CH:24]=2)=[CH:9][CH:8]=1)[CH2:3][CH2:4][CH2:5][CH3:6]

参加物

5

反応物 3

HCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 27355991-Bromo-4-pentylbenzeneHCID 5462224Magnesium

生成物 1

HCID 229258984-n-Pentyl-4'-benzyloxybiphenyl収率 62%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Magnesium (1.06 g: 88.3 mmol) and 4-n-pentylbromobenzene (10.0 g: 44.01 mmol) were dissolved in 50 ml of dried tetrahydrofuran, and a Grignard reagent was prepared from the mixture. To the Grignard reagent was added 11.6 g (44.1 mmol) of 4-(benzyloxy)bromobenzene synthesized in the step (i). The reaction system was purged with argon. To the reaction system was added 600 mg of dichloro(1,4-diphenylphosphinobutane)palladium (II) [Pd(dppb)Cl2], and the reaction was conducted for 24 hours. The reaction mixture was poured into an iced water, and the resultant mixture was acidified by adding hydrochloric acid. The resultant solid was collected by filtration, washed with water, dried, and recrystallized from a mixed solvent of hexane/toluene to give 9.0 g (27.3 mmol) of 4-n-pentyl-4′-benzyloxybiphenyl.

後処理

  1. customsynthesized in the step (i)
  2. customThe reaction system was purged with argon
  3. additionTo the reaction system was added 600 mg of dichloro(1,4-diphenylphosphinobutane)palladium (II) [Pd(dppb)Cl2]
  4. additionThe reaction mixture was poured into an iced water
  5. additionby adding hydrochloric acid
  6. filtrationThe resultant solid was collected by filtration
  7. washwashed with water
  8. customdried
  9. customrecrystallized from a mixed solvent of hexane/toluene

出典と根拠

ORDレコード
ord-8d20c04849414269beea7df1f151b610
出典データセット
uspto-grants-2009_05
特許番号
US07534547B2

反応ノート

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