Water → 2-Hydroxy-5-(4'-hexylbiphenyl-4-yl)thiophene

HRID 2121308Notes

Reaction equation

HRID 2121308 reaction equation
B(Br)(Br)Br.C([O:8][C:9]1[S:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)=[CH:12][CH:13]=1)CC.O>ClCCl>[OH:8][C:9]1[S:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 234321112-Propyloxy-5-(4'-hexylbiphenyl-4-yl)thiophene

Product 1

HCID 234321732-Hydroxy-5-(4'-hexylbiphenyl-4-yl)thiophene

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-propyloxy-5-(4′-hexylbiphenyl-4-yl)thiophene [Zh. Org. Khim., (1979) Vol. 49, pp. 476] (1.0 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 0.4 g of g 2-hydroxy-5-(4′-hexylbiphenyl-4-yl)thiophene.

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-ce4690ac65f343cebdf98853a4762f5b
Source dataset
uspto-grants-2004_02
Patent number
US06696110B1

Reaction notes

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