Water → 1-(4-Hydroxyphenyl)-2-(2-cyanothiophen-5-yl)acetylene

HRID 2121312Notes

Reaction equation

HRID 2121312 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[S:19][C:18]([C:20]#[N:21])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1.O>ClCCl>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[C:14][C:15]2[S:19][C:18]([C:20]#[N:21])=[CH:17][CH:16]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 234322581-(4-Methoxyphenyl)-2-(2-cyanothiophen-5-yl)acetylene

Product 1

HCID 234322421-(4-Hydroxyphenyl)-2-(2-cyanothiophen-5-yl)acetyleneYield 63.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1M solution of boron tribromide in dichloromethane (75 cm3) is added dropwise to a solution of 1-(4-methoxyphenyl)-2-(2-cyanothiophen-5-yl)acetylene (3.0 g) and dichloromethane (100 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/ethyi acetate mixture as eluent and recrystallisation from ethanol to yield 1.8 g of g 1-(4-hydroxyphenyl)-2-(2-cyanothiophen-5-yl)acetylene.

Workup

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

Sources & evidence

ORD record
ord-621644abffbf4138b1cbb5365c7f7f15
Source dataset
uspto-grants-2004_02
Patent number
US06696110B1

Reaction notes

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