1,4-Dibromobutane → HCID 18533207, compound

HRID 413429Notes

Reaction equation

HRID 413429 reaction equation
[C:1]([O:5][C:6]1[CH:7]=[C:8]([CH2:12][OH:13])[CH:9]=[CH:10][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[Br:14][CH2:15][CH2:16][CH2:17][CH2:18]Br>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].C1C=CC=CC=1>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][O:13][CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH:7]=1

Participants

6

Reactant 2

HCID 80561,4-DibromobutaneHCID 23269370(3-TERT-BUTOXY-PHENYL)-METHANOL

Product 1

HCID 18533207HCID 18533207, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 241BenzeneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of (3-tert-butoxy-phenyl) methanol (4.02 g, 0.022 mol) and tetrabutylammonium hydrogen sulfate (0.379 g, 0.00115 mol) in 50% NaOH solution (6 mL) and benzene (15 mL) Was added 1,4-dibromobutane (7.99 mL, 0.067 mol) with vigorous stirring at ambient temperature. After stirring for 8 h, the mixture was partitioned between H2O and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered, and concentrated to give the title compound after purification on an ISCO Combiflash eluting with 0-10% EtOAc/hexane.

Workup

  1. stirringAfter stirring for 8 h
  2. customthe mixture was partitioned between H2O and EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d21e192f33ef4a03bf5bf6b6b837323d
Source dataset
uspto-grants-2003_05
Patent number
US06566385B2

Reaction notes

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