Boron tribromide → 4-Chloro-2-(2,6-dichloro-4-hydroxyphenyl)-1-methyl-1H-indol-6-ol

HRID 543206Notes

Reaction equation

HRID 543206 reaction equation
B(Br)(Br)Br.[CH3:5][N:6]1[C:14]2[C:9](=[C:10]([Cl:17])[CH:11]=[C:12]([O:15]C)[CH:13]=2)[CH:8]=[C:7]1[C:18]1[C:23]([Cl:24])=[CH:22][C:21]([O:25]C)=[CH:20][C:19]=1[Cl:27]>O>[CH3:5][N:6]1[C:14]2[C:9](=[C:10]([Cl:17])[CH:11]=[C:12]([OH:15])[CH:13]=2)[CH:8]=[C:7]1[C:18]1[C:19]([Cl:27])=[CH:20][C:21]([OH:25])=[CH:22][C:23]=1[Cl:24]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 13057490HCID 13057490, compound

Product 1

HCID 549944-Chloro-2-(2,6-dichloro-4-hydroxyphenyl)-1-methyl-1H-indol-6-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.4 ml (35 mmole) of BBr3 were added with a syringe to a solution of 3.0 grams of 1-methyl-2-(2,6-dichloro-4-methoxy-phenyl)-4-chloro-6-methoxy-indole in 50 ml of water free methylene chloride at -70° C. After 30 minutes the cold bath was removed and the mixture was stirred overnight. The reaction mixture under ice cooling was carefully poured into a saturated aqueous sodium bicarbonate solution. The precipitate was filtered off with suction, washed with water and reprecipitated from methanol/water. Yield: 2.4 grams.

Workup

  1. customAfter 30 minutes the cold bath was removed
  2. additionThe reaction mixture under ice cooling was carefully poured into a saturated aqueous sodium bicarbonate solution
  3. filtrationThe precipitate was filtered off with suction
  4. washwashed with water
  5. customreprecipitated from methanol/water

Sources & evidence

ORD record
ord-97d13017c0634a87a13ebaa65af231a2
Source dataset
uspto-grants-1987_04
Patent number
US04661511

Reaction notes

Loading…