4-Fluorobenzyl chloride → HCID 877022, compound

HRID 1095169Notes

Reaction equation

HRID 1095169 reaction equation
[Br: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+].Cl[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 96024-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 728635-Bromosalicylaldehyde

Product 1

HCID 877022HCID 877022, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a mixture of 5-bromo-2-hydroxy-benzaldehyde (5 g, 25 mmol), KI (2 g) and K2CO3 (7 g, 50 mmol) in DMF (100 mL) was added 1-chloromethyl-4-fluoro-benzene (3.96 g, 28 mmol). The mixture was heated at 140° C. for 2 h, then cooled to room temperature, partitioned between water and ethyl acetate. The organic layer was washed with water for 3 times, dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography to give the title compound (4.5 g).

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between water and ethyl acetate
  3. washThe organic layer was washed with water for 3 times
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0b152b0bc3864046980732d82348d552
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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