Boron tribromide → HCID 21549163, compound

HRID 1605110Notes

Reaction equation

HRID 1605110 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1([Cl:18])[CH2:8][C:7]1([C:10]1[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=1)[CH3:9]>C(Cl)Cl>[Cl:5][C:6]1([Cl:18])[CH2:8][C:7]1([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[CH3:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 23272398HCID 23272398, compound

Product 1

HCID 21549163HCID 21549163, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6.1 g. (0.0242 mole) of boron tribromide in 25 ml. of methylene dichloride was added dropwise to a stirred solution of 6.1 g. (0.0264 mole) of p-(2,2-dichloro-1-methylcyclopropyl)anisole in 25 ml. of methylene dichloride cooled in an ice bath. The reaction mixture was stirred at 0° for one hour, then the ice bath was removed and the mixture stirred for an additional one hour. The reaction mixture was quenched in ice water and the layers separated. The aqueous layer was extracted with methylene dichloride, and the combined methylene dichloride solutions were washed with water and with dilute sodium hydroxide solution. At this point the sodium salt of p-(2,2-dichloro-1-methylcyclopropyl)phenol separated and was collected by filtration. The filter cake was combined with the original aqueous layer and acidified with concentrated hydrochloric acid. The acidified solution was extracted with ether and the ether dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was recrystallized from carbon tetrachloride to give p-(2,2-dichloro-1-methylcyclopropyl)phenol, m.p. 125°-126°C.

Workup

  1. customthe ice bath was removed
  2. stirringthe mixture stirred for an additional one hour
  3. customThe reaction mixture was quenched in ice water
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted with methylene dichloride
  6. washthe combined methylene dichloride solutions were washed with water and with dilute sodium hydroxide solution
  7. customAt this point the sodium salt of p-(2,2-dichloro-1-methylcyclopropyl)phenol separated
  8. filtrationwas collected by filtration
  9. extractionThe acidified solution was extracted with ether
  10. dry with materialthe ether dried over anhydrous sodium sulfate
  11. concentrationconcentrated in vacuo
  12. customThe residue was recrystallized from carbon tetrachloride

Sources & evidence

ORD record
ord-56c49d080848404782e35a77da1a31d5
Source dataset
uspto-grants-1976_04
Patent number
US03948973

Reaction notes

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