Sodium Carbonate → 4-(2-Benzyloxy ethoxy)-2-bromobenzaldehyde

HRID 339625Notes

Reaction equation

HRID 339625 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][CH2:25][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][CH2:25][CH2:26][O:27][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([Br:1])[CH:9]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 121412-(Benzyloxy) ethanolHCID 27733192-Bromo-4-fluorobenzaldehyde

Product 1

HCID 866341464-(2-Benzyloxy ethoxy)-2-bromobenzaldehyde

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-bromo-4-fluoro-benzaldehyde (32.0 g, 157 mmol), Na2CO3 (85.5 g, 788 mmol), and 2-benzyloxy ethanol (24.0 g, 158 mmol) in anhydrous DMSO (300 mL) were heated under N2 at 130° C. (bath temp) for 18 h. The reaction mixture cooled to rt, diluted with H2O (100 mL), 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 10% EtOAc in hexane) to give the title compound as a viscous liquid: yield 11.8 g (22%).

Workup

  1. temperatureThe reaction mixture cooled to rt
  2. extractionextracted with EtOAc The organic layer
  3. washwas washed with H2O
  4. dry with materialbrine, dried (MgSO4)
  5. concentrationconcentrated in vacuo The residue
  6. customwas purified by flash chromatography (hexane to 10% EtOAc in hexane)

Sources & evidence

ORD record
ord-d2170770d95849578ce7009a51e02cf7
Source dataset
uspto-grants-2014_11
Patent number
US08895534B2

Reaction notes

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