Boron tribromide → HCID 58292554, compound

HRID 1798064Notes

Reaction equation

HRID 1798064 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, compound

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 dropwise boron tribromide (18.75 g, 75.0 mmol) at −78° C. The reaction mixture was stirred at room temperature overnight, poured into ice and extracted with ethyl acetate (80 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (EtOAc/PE=1/3) on silica gel to give the title compound as a white solid. (5.09 g, Y: 78.2%). 1H NMR (400 MHz, DMSO-d) δ12.18 (s, 1H), 11.33 (s, 1H), 9.98 (s, 1H), 6.71-6.72 (d, J=2.4 Hz, 1H), 6.30-6.31 (d, J=2 Hz, 1H). MS (ESI) m/z=217 [M+H]+.

Workup

  1. additionpoured into ice
  2. extractionextracted with ethyl acetate (80 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (EtOAc/PE=1/3) on silica gel

Sources & evidence

ORD record
ord-7c53238a3bcb4073abbd51552420fdec
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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