Sodium Carbonate → 2-Benzyloxy propoxy-2-bromobenzaldehyde

HRID 339626Notes

Reaction equation

HRID 339626 reaction equation
[Br:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[Na+].[Na+].[CH2:17]([O:24][CH:25]([CH3:28])[CH2:26][OH:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CS(C)=O.O>[CH2:17]([O:24][CH:25]([CH3:28])[CH2:26][O:27][C:9]1[C:2]([Br:1])=[C:3]([CH:6]=[CH:7][CH:8]=1)[CH:4]=[O:5])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5618252-(Benzyloxy)propan-1-olHCID 27733192-Bromo-4-fluorobenzaldehyde

Product 1

HCID 866341472-Benzyloxy propoxy-2-bromobenzaldehyde

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-bromo-4-fluoro-benzaldehyde (30.0 g, 148 mmol), Na2CO3 (78.31 g, 738.8 mmol) and 2-benzyloxy propanol (24.56 g, 147.8 mmol) in anhydrous DMSO (300 mL) was heated with stirring at 130° C. (bath temp) for 72 h under N2. The reaction mixture was cooled to rt and diluted with H2O and extracted with EtOAc. The organic layer was washed with H2O then brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (hexane to 30% EtOAc in hexane) to give the title compound: yield 3.84 g (7%).

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled to rt
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with H2O
  5. dry with materialbrine, dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (hexane to 30% EtOAc in hexane)

Sources & evidence

ORD record
ord-3af1b686eead4d5a8969e3b6016b1e49
Source dataset
uspto-grants-2014_11
Patent number
US08895534B2

Reaction notes

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