Water → 2-(4-Hydroxyphenyl)-5-octylthiazole

HRID 2121302Notes

Reaction equation

HRID 2121302 reaction equation
B(Br)(Br)Br.C([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][C:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:17][N:18]=2)=[CH:10][CH:9]=1)C.O>ClCCl>[OH:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[S:15][C:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:17][N:18]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 234320272-(4-Ethoxyphenyl)-5-octylthiazole

Product 1

HCID 1358448422-(4-Hydroxyphenyl)-5-octylthiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1M solution of boron tribromide in dichloromethane (50 cm3) is added dropwise to a solution of 2-(4-ethoxyphenyl)-5-octylthiazole [J. prakt. Chem., (1979) Vol. 321, pp 643](2.0 g) and dichloromethane (50 cm3) at 0° C. under an atmosphere of nitrogen. The reaction solution is stirred overnight and water (100 cm3) added. The organic layer is separated off and the aqueous layer extracted with dichloromethane (2×100 cm3). The combined organic layers are washed with brine (2×100 cm3) and then dried (MgSO4), filtered and evaporated down. The residue is purified by column chromatography on silica gel using a 9:1 hexane/ethyl acetate mixture as eluent and recrystallisation from ethanol to yield 1.0 9 of g 2-(4-hydroxyphenyl)-5-octylthiazole.

Workup

  1. customat 0° C.
  2. customThe organic layer is separated off
  3. extractionthe aqueous layer extracted with dichloromethane (2×100 cm3)
  4. washThe combined organic layers are washed with brine (2×100 cm3)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated down
  8. customThe residue is purified by column chromatography on silica gel using a 9:1 hexane/ethyl acetate mixture as eluent
  9. customrecrystallisation from ethanol

Sources & evidence

ORD record
ord-09f4ab30b33049959982c895c96572a4
Source dataset
uspto-grants-2004_02
Patent number
US06696110B1

Reaction notes

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