Boron tribromide → HCID 58292554, compound

HRID 1798071Notes

Reaction equation

HRID 1798071 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([O:10]C)[CH:7]=[C:6]([O:12]C)[C:3]=1[CH:4]=[O:5].B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([OH:12])[C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 114023032-Bromo-4,6-dimethoxybenzaldehyde

Product 1

HCID 58292554HCID 58292554, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-4,6-dimethoxybenzaldehyde (7.35 g, 30.0 mmol) in dichloromethane (50 mL) was added boron tribromide (18.7 g, 75.0 mmol) dropwise at −78° C. The reaction mixture was stirred at room temperature overnight and poured onto ice. The resulting mixture was extracted with ethyl acetate (3×80 mL) and the combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuo. The residue was purified by column chromatography on silica gel (EtOAc:PE=1:1) to give the title compound as a white solid (5.10 g, Yield: 78.2%). 1H NMR (400 MHz, DMSO-d) δ 12.18 (s, 1H), 11.32 (s, 1H), 9.98 (s, 1H), 6.71-6.72 (d, J=2.4 Hz, 1H), 6.30-6.31 (d, J=2.0 Hz, 1H).

Workup

  1. additionpoured onto ice
  2. extractionThe resulting mixture was extracted with ethyl acetate (3×80 mL)
  3. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (EtOAc:PE=1:1)

Sources & evidence

ORD record
ord-c1a01395c9a0448aab7181073c5a9c43
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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