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

HRID 493038Notes

Reaction equation

HRID 493038 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 229258984-n-Pentyl-4'-benzyloxybiphenylYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8d20c04849414269beea7df1f151b610
Source dataset
uspto-grants-2009_05
Patent number
US07534547B2

Reaction notes

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