Dimethylboronbromide → 1,1-Bis(2-hydroxyphenyl)cyclopropane

HRID 466917Notes

Reaction equation

HRID 466917 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18]C)[CH2:11][CH2:10]1.BrB(C)C>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[OH:18])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 123224DimethylboronbromideHCID 148397041,1-Bis(2-methoxyphenyl)cyclopropane

Product 1

HCID 148397051,1-Bis(2-hydroxyphenyl)cyclopropane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Bis(2-methoxyphenyl)cyclopropane (10.0 g, 0.039 mole) was combined with 60 ml of dichloromethane and the mixture was cooled in an ice bath and then treated with 10.0 ml of bromodimethylborane with cooling and stirring. The starting material was consumed in less than 1 hour as determined by gas-liquid chromatography. The mixture was then diluted with 500 ml of ether and the resulting solution was extracted twice with water and then with water saturated with ammonium chloride, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain 9.0 g (101 percent of theory) of the title compound as a brownish-black solid; m.p., 158°-160° C. This eluted as one clean peak in gas-liquid chromatography and had a proton NMR spectrum consistent with the assigned structure.

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. temperaturewith cooling
  3. customThe starting material was consumed in less than 1 hour
  4. additionThe mixture was then diluted with 500 ml of ether
  5. extractionthe resulting solution was extracted twice with water
  6. dry with materialwith water saturated with ammonium chloride, dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-ced3c9d0286a40f5897a6bc492b63fbd
Source dataset
uspto-grants-1992_10
Patent number
US05158597

Reaction notes

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