Boron tribromide → 5-Hydroxybenzocyclobutene-1-carboxylic acid methyl ester

HRID 1248363Notes

Reaction equation

HRID 1248363 reaction equation
B(Br)(Br)Br.[CH3:5][O:6][C:7]([C:9]1[C:12]2[CH:13]=[C:14]([O:17]C)[CH:15]=[CH:16][C:11]=2[CH:10]=1)=[O:8]>ClCCl>[CH3:5][O:6][C:7]([C:9]1[C:12]2[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:11]=2[CH:10]=1)=[O:8]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 541184135-Methoxybenzocyclobutene-1-carboxylic acid methyl ester

Product 1

HCID 536353185-Hydroxybenzocyclobutene-1-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1000 ml of a 1-molar solution of boron tribromide in dichloromethane are poured over 19.5 g of 5-methoxybenzocyclobutene-1-carboxylic acid methyl ester and the whole is heated at reflux for 6 hours. The whole is concentrated to dryness by evaporation and extracted by shaking with a mixture of 2000 ml of dichloromethane and 1000 ml of water and the organic phase is separated off, washed with water, dried over magnesium sulphate and concentrated to dryness by evaporation. 5-hydroxybenzocyclobutene-1-carboxylic acid methyl ester is obtained in the form of white crystals having a melting point of 108°-109° (from ether/hexane).

Workup

  1. temperaturethe whole is heated
  2. temperatureat reflux for 6 hours
  3. concentrationThe whole is concentrated to dryness by evaporation
  4. extractionextracted
  5. customthe organic phase is separated off
  6. washwashed with water
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated to dryness by evaporation

Sources & evidence

ORD record
ord-9a66093b66e84320ab9db742667f478b
Source dataset
uspto-grants-1985_06
Patent number
US04523030

Reaction notes

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