Benzyl Bromide → HCID 67465459, compound

HRID 1777718Notes

Reaction equation

HRID 1777718 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[Cl:10].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+]>CN(C=O)C>[Cl:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[N:1]([CH2:6][C:5]1[CH:8]=[CH:9][CH:2]=[CH:3][CH:4]=1)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]#[N:7]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 5198964-Amino-3-chlorobenzonitrile

Product 1

HCID 67465459HCID 67465459, compoundYield 191.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-amino-3-chlorobenzonitrile (1.0 g, 6.56 mmol, 1 eq) and benzyl bromide (3.12 mL, 26.2 mmol, 4.0 eq) in dry DMF (10 mL) was added at rt NaH (1.31 g, 32.8 mmol, 5 eq) portionwise under Ar(g). The reaction mixture was stirred at rt overnight, and was subsequently partitioned with H2O (30 mL) and extracted with EtOAc (5×20 mL) and CH2Cl2 (20 mL). The combined organic extracts were dried over MgSO4 and the solvent was removed in vacuo. The residue was further purified by silica gel column chromatography with hexane/EtOAc (1:0-9:1) to furnish 2 as a white solid (2.09 g, 96%).

Workup

  1. customwas subsequently partitioned with H2O (30 mL)
  2. extractionextracted with EtOAc (5×20 mL) and CH2Cl2 (20 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. customthe solvent was removed in vacuo
  5. customThe residue was further purified by silica gel column chromatography with hexane/EtOAc (1:0-9:1)

Sources & evidence

ORD record
ord-433f7b527cd64f0f88f5d737c8955cf5
Source dataset
uspto-grants-2016_02
Patent number
US09266879B2

Reaction notes

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