Benzyl Bromide → HCID 22600477, compound

HRID 1760061Notes

Reaction equation

HRID 1760061 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[CH:17]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:18]([O:20][CH3:21])=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 23665647Potassium tert-butoxideHCID 69744622HCID 69744622, compound

Product 1

HCID 22600477HCID 22600477, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.6 g (16.3 mmol) of methyl (2-benzyloxy-5-cyano-phenyl)-acetate are dissolved in 10 ml of dimethylformamide and 1.9 g (17 mmol) of potassium tert. butoxide are added. Then 2 ml (16.8 mmol) of benzylbromide are added dropwise while cooling gently with ice and the mixture is then stirred for another two hours at ambient temperature. It is stirred with ice water and extracted with ethyl acetate. The combined organic extracts are dried and concentrated by evaporation. The crude product is chromatographed on silica gel, eluting with petroleum ether/ethyl acetate (0-7%).

Workup

  1. temperaturewhile cooling gently with ice
  2. extractionextracted with ethyl acetate
  3. customThe combined organic extracts are dried
  4. concentrationconcentrated by evaporation
  5. customThe crude product is chromatographed on silica gel
  6. washeluting with petroleum ether/ethyl acetate (0-7%)

Sources & evidence

ORD record
ord-75527a6142694d538b39e94c1335c504
Source dataset
uspto-grants-2005_01
Patent number
US06838565B2

Reaction notes

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