Benzyl Chloride → 2-(Benzyloxy)-4-fluorobenzaldehyde

HRID 18170

Reaction equation

HRID 18170 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([OH:10])[CH:3]=1.[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O.O>CN(C=O)C>[CH2:11]([O:10][C:4]1[CH:3]=[C:2]([F:1])[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 27792684-Fluoro-2-hydroxybenzaldehydeHCID 22728543Water ethylacetate

Product 1

HCID 106809572-(Benzyloxy)-4-fluorobenzaldehydeYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-fluoro-2-hydroxy-benzaldehyde (560 mg, 4 mmol) in DMF (10 ml) were added benzyl chloride (0.5 ml, 4.33 mmol), and K2CO3 (860 mg, 6.22 mmol). After heating at reflux for an hour, the reaction mixture was allowed to cool to room temperature and was poured into a mixture of EtOAc/H2O. The organic layer was separated, washed with H2O and dried over MgSO4. The resulting oil was purified by flash chromatography to give 2-benzyloxy-4-fluoro-benzaldehyde as pale oil (628 mg, 68%), 1H NMR (CDCl3, 300 MHz) δ: 5.17 (s, 2H), 6.74 (m, 2H), 7.36 (m, 5H), 7.88 (m, 1H), 10.51 (s, 1H).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for an hour
  3. customThe organic layer was separated
  4. washwashed with H2O
  5. dry with materialdried over MgSO4
  6. customThe resulting oil was purified by flash chromatography

Sources & evidence

ORD record
ord-bab34257f35f44208f93b82c012ad71a
Source dataset
uspto-grants-2010_06
Patent number
US07741326B2

Linked notes

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