Bromoacetonitrile → Tert-butyl 3-(3-chlorophenyl)-3-(cyanomethoxy)propyl(methyl)carbamate

HRID 426035Notes

Reaction equation

HRID 426035 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:10]([OH:22])[CH2:11][CH2:12][N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:7]=[CH:8][CH:9]=1.Br[CH2:24][C:25]#[N:26].[NH4+].[Cl-]>CC#N.C(OCC)(=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([CH:10]([O:22][CH2:24][C:25]#[N:26])[CH2:11][CH2:12][N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59364384Tert-butyl 3-(3-chlorophenyl)-3-hydroxypropyl(methyl)carbamate

Product 1

HCID 66704520Tert-butyl 3-(3-chlorophenyl)-3-(cyanomethoxy)propyl(methyl)carbamate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of NaH (0.65 g, 27 mmol) and tert-butyl 3-(3-chlorophenyl)-3-hydroxypropyl(methyl)carbamate (2.7 g, 9 mmol) in CH3CN (60 mL) at 0-5° C. was added drop wise a solution of bromoacetonitrile (3.3 g, 27 mmol) in CH3CN (20 mL), the reaction mixture was stirred for overnight at room temperature. The reaction mixture was poured into saturated aqueous NH4Cl, ethyl acetate (50 mL) was added. The organic layer was washed with water (3×20 mL) and brine, dried over Na2SO4, filtered and concentrated in vacuo to afford the crude product, which was used for the next step without purification.

Workup

  1. additionwas added
  2. washThe organic layer was washed with water (3×20 mL) and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3d5eb7d784cb4b3abe02f9735e8eadf2
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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