Boron tribromide → HCID 20458173, compound

HRID 544727Notes

Reaction equation

HRID 544727 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][C:3]=1[N:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1.CC(C)=O.C(=O)=O.B(Br)(Br)Br>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 18522661Acetone cardiceHCID 20458193HCID 20458193, compound

Product 1

HCID 20458173HCID 20458173, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 86.6 g (0.46 mole) of 4-methyl-3-(pyrrol-1-yl)-anisole in 1.5 liters of absolute methylene chloride is cooled to -78° with acetone/dry ice. At this temperature, 231.7 g (0.92 mole) of boron tribromide are added dropwise. Subsequently, the cooling bath is removed and the reaction mixture is heated to from 0° to 5°, then poured into 2 liters of ice/water, and the methylene chloride phase is removed and washed with saturated sodium chloride solution. The aqueous phases are then extracted a further twice with methylene chloride. The organic phases are combined, dried over sodium sulphate and concentrated in a vacuum rotary evaporator. Distillation of the residue in a high vacuum yields 4-methyl-3-(pyrrol-1-yl)-phenol, b.p. 105°-107°/0.03 torr, Rf (toluene/ethyl acetate=10:1): 0.38.

Workup

  1. customSubsequently, the cooling bath is removed
  2. temperaturethe reaction mixture is heated to from 0° to 5°
  3. additionpoured into 2 liters of ice/water
  4. customthe methylene chloride phase is removed
  5. washwashed with saturated sodium chloride solution
  6. extractionThe aqueous phases are then extracted a further twice with methylene chloride
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated in a vacuum rotary evaporator
  9. distillationDistillation of the residue in a high vacuum

Sources & evidence

ORD record
ord-4804bde77f69453483ca09a9ef6cf8d7
Source dataset
uspto-grants-1984_05
Patent number
US04451462

Reaction notes

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