Benzoyl chloride → Benzo[b]thiophen-4-yl benzoate

HRID 2183622Notes

Reaction equation

HRID 2183622 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([OH:10])=[CH:7][CH:8]=[CH:9][C:2]1=2.[C:11](Cl)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[C:11]([O:10][C:6]1[C:3]2[CH:4]=[CH:5][S:1][C:2]=2[CH:9]=[CH:8][CH:7]=1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 19217Benzo(b)thiophen-4-ol

Product 1

HCID 21822894Benzo[b]thiophen-4-yl benzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of benzo[b]thiophen-4-ol (4 g), benzoyl chloride (3.3 ml) and pyridine (10 ml) was heated under reflux under nitrogen for 3 hours, then cooled to ambient temperature and poured onto ice-water (130 ml). The product was extracted into ether (3×50 ml), the combined extracts were washed with 5% aqueous sodium hydrogencarbonate solution (50 ml), 2M hydrochloric acid (50 ml) and water (3×50 ml), then they were dried (MgSO4) and the solvent was removed in vacuo to give benzo[b]thiophen-4-yl benzoate (6.7 g) as a cream solid which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under nitrogen for 3 hours
  3. additionpoured onto ice-water (130 ml)
  4. extractionThe product was extracted into ether (3×50 ml)
  5. washthe combined extracts were washed with 5% aqueous sodium hydrogencarbonate solution (50 ml), 2M hydrochloric acid (50 ml) and water (3×50 ml)
  6. dry with materialthey were dried (MgSO4)
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a16b3407552c49b1b9285cb589d28545
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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