Sodium Methoxide → HCID 67979452, compound

HRID 539312Notes

Reaction equation

HRID 539312 reaction equation
Br[CH2:2][C:3]1[C:4]([F:11])=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[CH3:12][O-:13].[Na+]>CO>[F:11][C:4]1[C:3]([CH2:2][O:13][CH3:12])=[CH:10][CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 666784653-(Bromomethyl)-2-fluorobenzonitrile2×

Product 1

HCID 67979452HCID 67979452, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(Bromomethyl)-2-fluorobenzonitrile (Intermediate 84, 1.39 g, 6.49 mmol) was dissolved in MeOH (10 mL) and sodium methoxide (1.238 mL, 6.49 mmol) was added. The mixture was stirred at r.t. for 2 h. This mixture was concentrated and then partitioned between water and EtOAc. The organic layer was separated and then concentrated in vacuo. The resulting residue was purified by flash chromatography using EtOAc/heptanes as eluent to give the title compound (0.900 g, 84% yield): 1H NMR (500 MHz, DMSO-d6) δ ppm 3.32 (s, 3 H) 4.52 (br. s, 2 H) 7.42 (t, 1 H) 7.77-7.84 (m, 1 H) 7.86-7.92 (m, 1 H); MS (EI) m/z 166 M+.

Workup

  1. concentrationThis mixture was concentrated
  2. custompartitioned between water and EtOAc
  3. customThe organic layer was separated
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-94cb9fe8f54c42e09c159ae346d084e9
Source dataset
uspto-grants-2014_10
Patent number
US08865911B2

Reaction notes

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