Boron tribromide → HCID 58292554, compound

HRID 1798260Notes

Reaction equation

HRID 1798260 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 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-4,6-dimethoxy-benzaldehyde (5.83 g, 23.9 mmol) in dichloromethane (50 mL) was added BBr3 (6.78 mL, 71.7 mmol) at −78° C. The reaction was stirred at room temperature overnight and poured into ice slowly. The resulting mixture was extracted with ethyl acetate. The organic layer was separated, dried (Na2SO4), and concentrated. The residue was purified by flash column chromatography (silica, hexanes/ethyl acetate=2:1) to give the title compound (4.84 g, 94%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 12.2 (s, 1H), 11.3 (br, 1H), 10.0 (s, 1H), 6.75 (d, J=2.1 Hz, 1H), 6.33 (d, J=2.1 Hz, 1H).

Workup

  1. additionpoured into ice slowly
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (silica, hexanes/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-0c649e560cb543d08b4651bb9081ec52
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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