Boron tribromide → HCID 57353809, compound

HRID 493183Notes

Reaction equation

HRID 493183 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([O:14]C)[CH:12]=[CH:13][C:7]=2[CH:6]=1)=[O:4].B(Br)(Br)Br>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([OH:14])[CH:12]=[CH:13][C:7]=2[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 534861116-Methoxy-benzo[B]thiophene-2-carboxylic acid methyl ester

Product 1

HCID 57353809HCID 57353809, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The above prepared 6-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester (0.200 g, 0.900 mmol) was dissolved in 5.5 mL of CH2Cl2, cooled to 0° C., and treated with BBr3 (1.90 mL of 1M solution in CH2Cl2, 2 eq.). After 3 additional h at ambient temperature, the reaction mixture was carefully poured onto crashed ice, twofold extracted with AcOEt, washed with water and brine, dried over magnesium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=8/2) gave 0.061 g of the title compound as light brown solid.

Workup

  1. additionAfter 3 additional h at ambient temperature, the reaction mixture was carefully poured
  2. extractiontwofold extracted with AcOEt
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-53507a3e520241fba063e6aef9fa7011
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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