Boron trifluoride etherate → 6,7-Dichloro-5-methoxybenzo[b]thiophene

HRID 370938

Reaction equation

HRID 370938 reaction equation
[Cl:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]2[CH:9](O)[CH2:8][S:7][C:6]=2[C:11]=1[Cl:12].B(F)(F)F.CCOCC.[OH-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[C:11]=1[Cl:12]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 132902146,7-Dichloro-2,3-dihydro-3-hydroxy-5-methoxybenzo[b]thiophene

Product 1

HCID 132899966,7-Dichloro-5-methoxybenzo[b]thiopheneYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.7 g of 6,7-dichloro-2,3-dihydro-3-hydroxy-5-methoxybenzo[b]thiophene, 1 ml of boron trifluoride etherate and 4 ml of glacial acetic acid is heated at 100° for 5 min. Ice is added and the mixture is basified with dilute sodium hydroxide solution. The off-white solid is collected or a filter, air-dried and recrystallized from ether-hexane to give 0.65 g of 6,7-dichloro-5-methoxybenzo[b]thiophene as prisms, mp 103°-104.5°.

Workup

  1. temperatureis heated at 100° for 5 min
  2. additionIce is added
  3. customThe off-white solid is collected
  4. customa filter, air-dried
  5. customrecrystallized from ether-hexane

Sources & evidence

ORD record
ord-a7a1e58dfbae40dcbc89bd7f1a4472f8
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Linked notes

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