Dimethylformamide → 1-Bromo-4-(cyclopentyloxy)benzene

HRID 646160Notes

Reaction equation

HRID 646160 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH:9]1(Br)[CH2:13][CH2:12][CH2:11][CH2:10]1.[OH-].[Na+].CN(C=O)C>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78084-BromophenolHCID 8728BromocyclopentaneHCID 14798Sodium Hydroxide

Product 1

HCID 225999581-Bromo-4-(cyclopentyloxy)benzeneYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromophenol (40 g, 231 mmol), cyclopentylbromide (50 ml, 462 mmol), NaOH (18.5 g, 462 mmol) and DMF (150 mL) was stirred at 100° C. for 13.5 h, poured into water (300 mL) and extracted with t-BuOMe (4×100 mL). The combined organic extracts were washed with water (2×100 mL), brine, dried (Na2SO4), concentrated and distilled in vacuo to yield the sub-title compound (46.4 g, 94%).

Workup

  1. extractionextracted with t-BuOMe (4×100 mL)
  2. washThe combined organic extracts were washed with water (2×100 mL), brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-086d9978a4d5402bab39e3320b0c5362
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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