1-Bromopentane → 3-Bromophenol

HRID 439761

Reaction equation

HRID 439761 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH2:16]([O:8][CH2:4][CH2:5][CH2:6][CH2:7][CH3:2])[CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 3

HCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 115633-Bromophenol

Product 2

HCID 115633-BromophenolHCID 12743Pentyl ether

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5.0 gm of 3-Bromophenol in 60 mls of dimethylformamide is added 6.0 gm of potassium carbonate followed by 4.3 ml of 1-bromopentane. This mixture is heated to 60° C. for 6 hours and then cooled to room temperature and filtered. The filtrate is diluted with ether and washed with water and brine. After drying over magnesium sulfate and concentrating, the crude oil obtained is chromatographed over silica gel, and eluted with 3:2 hexane:ether to yield 3-bromo-phenol, n-pentyl ether as a clear oil.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. additionThe filtrate is diluted with ether
  4. washwashed with water and brine
  5. dry with materialAfter drying over magnesium sulfate
  6. concentrationconcentrating
  7. customthe crude oil obtained
  8. customis chromatographed over silica gel
  9. washeluted with 3:2 hexane

Sources & evidence

ORD record
ord-797a315a2c754292b18ab6992c7363d2
Source dataset
uspto-grants-1996_05
Patent number
US05516767

Linked notes

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