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

HRID 1965064Notes

Reaction equation

HRID 1965064 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-321f846e955640749df791f13e5f839e
Source dataset
uspto-grants-2013_04
Patent number
US08415483B2

Reaction notes

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