Boron tribromide → HCID 68725520, compound

HRID 493190Notes

Reaction equation

HRID 493190 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:17]=[C:16]([O:18]C)[CH:15]=[CH:14][C:9]=2[C:10]=1[CH:11]([CH3:13])[CH3:12])=[O:5])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:9]=2[C:10]=1[CH:11]([CH3:13])[CH3:12])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68727007HCID 68727007, compound

Product 1

HCID 68725520HCID 68725520, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The above prepared 3-isopropyl-6-methoxy-benzofuran-2-carboxylic acid ethyl ester (2.52 g, 10 mmol) was dissolved in 65 mL of CH2Cl2, cooled to 0° C., and treated with BBr3 (19.2 mL of 1M solution in CH2Cl2, 2 eq.). After 1 h at 0° C. and one additional at ambient temperature, the reaction mixture was carefully poured onto crashed ice, twofold extracted with AcOEt, washed with water, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=8/2) afforded 0.930 g of the title compound as purple crystals.

Workup

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

Sources & evidence

ORD record
ord-88a5fc5ae5154bfda2c9189a4b98852e
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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