Boron tribromide → HCID 57675491, compound

HRID 490758Notes

Reaction equation

HRID 490758 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15]C)=[CH:12][CH:13]=2)[CH:8]=[C:7]1[CH3:17])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[CH3:17])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69054050HCID 69054050, compound

Product 1

HCID 57675491HCID 57675491, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of (5-methoxy-2-methyl-indol-1-yl)-acetic acid ethyl ester (0.87 g, 3.51 mmol) in methylene chloride (25 mL) is added BBr3 (1.0 mL, 10.5 mmol) at −20° C. After stirred at −20° C. for 2 hrs, the reaction mixture is poured into ice, extracted with methylene chloride, dried over sodium sulfate. Concentration yields the crude title compound, which is used for next step without further purification.

Workup

  1. additionthe reaction mixture is poured into ice
  2. extractionextracted with methylene chloride
  3. dry with materialdried over sodium sulfate
  4. concentrationConcentration

Sources & evidence

ORD record
ord-43d1528bbedc4b1e8398afe2f2f78f11
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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