Water → 2-Bromo-4,6-dimethoxybenzaldehyde

HRID 1798259Notes

Reaction equation

HRID 1798259 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[CH:3]=1.O=P(Cl)(Cl)Cl.O.CN([CH:21]=[O:22])C>>[Br:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([O:8][CH3:9])[C:7]=1[CH:21]=[O:22]

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 6391871-Bromo-3,5-dimethoxybenzene

Product 1

HCID 114023032-Bromo-4,6-dimethoxybenzaldehydeYield 65%

Conditions

Temperature
100 °C

Procedure

A solution of 1-bromo-3,5-dimethoxybenzene (10.0 g, 46.1 mmol) in DMF (40 mL) was treated with POCl3 (6.32 mL, 69.1 mmol) at 0° C. and heated to 100° C. for 6 h. The reaction was cooled to room temperature and water (40 mL) was added. The resulting mixture was heated to 50° C. 1 h. The reaction was cooled down and 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 (7.26 g, 65%). 1H NMR (300 MHz, CDCl3) δ 10.24 (s, 1H), 6.81 (s, 1H), 6.42 (s, 1H), 3.96 (s, 3H), 3.93 (s, 3H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. temperatureThe resulting mixture was heated to 50° C
  3. custom1 h
  4. temperatureThe reaction was cooled down
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue was purified by flash column chromatography (silica, hexanes/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-e219097788dc49dba2a345eb85bca8eb
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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