Bromoacetonitrile → HCID 22010418, compound

HRID 322941Notes

Reaction equation

HRID 322941 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15](=[O:24])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:32][C:33]#[N:34]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15](=[O:24])[CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[CH2:32][C:33]#[N:34])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11534Bromoacetonitrile2×HCID 10519489HCID 10519489, compoundHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 22010418HCID 22010418, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 1-(3-benzyloxyphenyl)-2-(2-methylphenyl)ethan-1-one (4 g) in tetrahydrofuran (100 mL) is treated with potassium tert-butoxide (200 mg). After stirring for 30 minutes, it is treated with bromoacetonitrile (0.98 mL), dropwise, and stirring is continued for a further 28 hours. The mixture is then treated with further quantities of potassium tert-butoxide (200 mg) and bromoacetonitrile (0.98 mL) and allowed to stand at room temperature overnight. It is then concentrated under reduced pressure and partitioned between water and ethyl acetate. The organic layer is dried over magnesium sulphate and evaporated, to give a brown oil, which is subjected to flash chromatography on silica gel, eluting with a mixture of ethyl acetate and pentane (1:9 v/v), to give 1-(3-benzyloxyphenyl)-3-cyano-2-(2-methylphenyl)propan-1-one, in the form of a colourless oil (0.67 g).

Workup

  1. stirringdropwise, and stirring
  2. waitis continued for a further 28 hours
  3. waitto stand at room temperature overnight
  4. concentrationIt is then concentrated under reduced pressure
  5. custompartitioned between water and ethyl acetate
  6. dry with materialThe organic layer is dried over magnesium sulphate
  7. customevaporated
  8. customto give a brown oil, which
  9. washeluting with a mixture of ethyl acetate and pentane (1:9 v/v)

Sources & evidence

ORD record
ord-220d0425645642f18eafba0495cab179
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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