Benzene, 1-(chloromethyl)-2-fluoro- → HCID 54068788, compound

HRID 345456Notes

Reaction equation

HRID 345456 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[OH:19])[C:5]([O:7][CH3:8])=[O:6].[F:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23]Cl.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[O:19][CH2:23][C:22]1[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=1[F:20])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 9580Benzene, 1-(chloromethyl)-2-fluoro-HCID 11430Potassium CarbonateHCID 136082962HCID 136082962, compound

Product 1

HCID 54068788HCID 54068788, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5 g (19 mmol) of methyl 1-hydroxy-2-naphthylglyoxylate O-methyloxime, 2.7 g (19 mmol) of 2-fluorobenzyl chloride and 2.6 g (19 mmol) of potassium carbonate in 65 ml of methanol are stirred under reflux for 8 h. The mixture is cooled to room temperature and the solids are removed by filtration. The filtrate is concentrated, and dilute sodium hydroxide solution is added. The mixture is then extracted by shaking several times with ether; the combined ether phases are washed with H2O, dried over sodium sulfate and concentrated. 5 g (13.6 mmol) of methyl 1-(2-fluorobenzyloxy)-2-naphthylglyoxylate O-methyloxime (yield 71%) are obtained (compound no. 2, Table 1).

Workup

  1. temperatureunder reflux for 8 h
  2. customthe solids are removed by filtration
  3. concentrationThe filtrate is concentrated
  4. additiondilute sodium hydroxide solution is added
  5. extractionThe mixture is then extracted
  6. washthe combined ether phases are washed with H2O
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-61a6e28c30344ad385271e27a20e4c1a
Source dataset
uspto-grants-1991_10
Patent number
US05057537

Reaction notes

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