Methanol → 3-Bromo-5-(methoxymethyl)benzonitrile

HRID 539300Notes

Reaction equation

HRID 539300 reaction equation
[CH3:1][OH:2].[H-].[Na+].[Br:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([CH2:14]Br)[CH:13]=1)[C:9]#[N:10]>CN(C=O)C>[Br:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([CH2:14][O:2][CH3:1])[CH:13]=1)[C:9]#[N:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 145678613-Bromo-5-(bromomethyl)benzonitrile

Product 1

HCID 679793983-Bromo-5-(methoxymethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

MeOH (0.088 mL, 2.18 mmol) was added to a slurry of NaH (45 mg, 1.13 mmol) in DMF (2 mL). When gas evolution ceased, a solution of 3-bromo-5-(bromomethyl)benzonitrile (see WO2009/100169; 240 mg, 0.87 mmol) in DMF (1 mL) was added. The reaction was quenched by adding aq. sat NH4Cl solution. The mixture was partitioned between toluene (5 mL) and water (3 mL). The toluene layer was collected, washed with water, dried over Na2SO4, and concentrated in vacuo. The crude product was dried at reduced pressure and used in the next step: GCMS (CI) m/z 226 [M+H]+.

Workup

  1. customThe reaction was quenched
  2. additionby adding aq.
  3. customThe mixture was partitioned between toluene (5 mL) and water (3 mL)
  4. customThe toluene layer was collected
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. dry with materialThe crude product was dried at reduced pressure

Sources & evidence

ORD record
ord-d98aad59c86b4906be8b6d18461f753c
Source dataset
uspto-grants-2014_10
Patent number
US08865911B2

Reaction notes

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