Water → 2-(Benzyloxy)-5-fluorobenzaldehyde

HRID 2036234Notes

Reaction equation

HRID 2036234 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C=O)C>[CH2:17]([O:10][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:9][C:6]=1[CH:7]=[O:8])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27373285-Fluorosalicylaldehyde

Product 1

HCID 107281542-(Benzyloxy)-5-fluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-fluoro-2-hydroxybenzaldehyde (5.0 g, 35.69 mmol, 1.00 eq.) and potassium carbonate (7.97 g, 57.10 mmol, 1.60 eq.) in DMF (60 mL), benzyl bromide (4.54 mL, 37.47 mmol, 1.05 eq.) was added dropwise. The reaction mixture was refluxed for 2 hours, then allowed to cool to r.t. and poured into 100 mL of cold water and extracted with AcOEt. The organic extract was washed with 10% aq. NaOH soln. and sat. aq. NaCl soln., dried over MgSO4 and concentrated in vacuo. The residue was purified by flash master (column: 100 g, flow: 45 mL/min, Heptane to Heptane+30% AcOEt) to yield 2-benzyloxy-5-fluoro-benzaldehyde as an yellow oil.

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction mixture was refluxed for 2 hours
  3. extractionextracted with AcOEt
  4. extractionThe organic extract
  5. washwas washed with 10% aq. NaOH soln
  6. dry with material, dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash master (column: 100 g, flow: 45 mL/min, Heptane to Heptane+30% AcOEt)

Sources & evidence

ORD record
ord-d512ea9b9df74892a4f158454a29287d
Source dataset
uspto-grants-2013_11
Patent number
US08575158B2

Reaction notes

Loading…