Boron tribromide → HCID 13772343, compound

HRID 1638982Notes

Reaction equation

HRID 1638982 reaction equation
[CH2:1]([C:8]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25]C)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH3:17])[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([C:8]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[OH:25])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH3:17])[C:9]1=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 13772341HCID 13772341, compound

Product 1

HCID 13772343HCID 13772343, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

25 g (0.073 mol) of 3-benzyl-1-methyl-3-(2-methoxyphenyl)- indolin-2-one are dissolved in 250 ml of methylene chloride. The solution is cooled to 0°-5° and a solution of 7 ml (0.074 mol) of boron tribromide in 50 ml of methylene chloride is added dropwise over the course of 30 minutes, and the mixture is then stirred at room temperature for 1 hour and poured onto ice-water. The organic phase is separated off, washed twice with water, dried over magnesium sulfate and concentrated. 17.8 g of crystalline product of melting point 188°-190° C. are obtained.

Workup

  1. temperatureThe solution is cooled to 0°-5°
  2. additionpoured onto ice-water
  3. customThe organic phase is separated off
  4. washwashed twice with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-23ae3ed7f03342cebe84cd9b295330bf
Source dataset
uspto-grants-1989_11
Patent number
US04882329

Reaction notes

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