Water → Methyl 3-(cyanomethyl)benzoate

HRID 1184812Notes

Reaction equation

HRID 1184812 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10]Br)[CH:5]=1.[C-:13]#[N:14].[Na+].O>CN(C=O)C>[C:13]([CH2:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([O:2][CH3:1])=[O:12])#[N:14]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 517981Methyl 3-(bromomethyl)benzoate

Product 1

HCID 10821136Methyl 3-(cyanomethyl)benzoateYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(bromomethyl)benzoic acid methyl ester (25 g, 109 mmol) in DMF (250 mL) was added NaCN (5.4 g, 109 mmol). The reaction mixture was stirred overnight at rt. The mixture was poured into water (1.5 L), followed by the extraction with TBME (2×500 mL). The combined organic layers were washed with water, brine, dried (Na2SO4), filtered and evaporated under reduced pressure to yield methyl 3-(cyanomethyl)benzoate 1 (17 g, 89%). 1H-NMR (400 MHz, CDCl3) 3.82 (s, 2H), 3.94 (s, 3H), 7.48 (m, 1H), 7.57 (m, 1H), 8.03 (m, 2H).

Workup

  1. extractionfollowed by the extraction with TBME (2×500 mL)
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b2cd9e623c3244e6a7127770dfed5f65
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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