1,4-Dibromobutane → HCID 18623176, compound

HRID 1721957Notes

Reaction equation

HRID 1721957 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[Br:11][CH2:12][CH2:13][CH2:14][CH2:15]Br.[OH-].[Na+]>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][O:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 80561,4-DibromobutaneHCID 14798Sodium HydroxideHCID 820684-Fluorophenethyl Alcohol

Product 1

HCID 18623176HCID 18623176, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

A mixture of 4-fluorobenzeneethanol (10.0 g), 1,4-dibromobutane (59.0 g), aqueous sodium hydroxide (50% w/v; 40 ml) and tetrabutylammonium bisulphate (1 g) was stirred at room temperature for 20 h, diluted with water (50 ml) and extracted with ER (2×100 ml). The dried extract was evaporated and the residue was purified by [C] eluting with cyclohexane followed by cyclohexane-ER (19:1) to give the title compound as a colourless oil (17.3 g). T.l.c. (cyclohexane-ER 9:1) Rf 0.4

Workup

  1. extractionextracted with ER (2×100 ml)
  2. extractionThe dried extract
  3. customwas evaporated
  4. customthe residue was purified by [C]
  5. washeluting with cyclohexane

Sources & evidence

ORD record
ord-4e46cb367b184d658e2231e33f0c506d
Source dataset
uspto-grants-1989_08
Patent number
US04853381

Reaction notes

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