Methanol → 4-Bromo-2-methoxy-3-methylbenzonitrile

HRID 1187002Notes

Reaction equation

HRID 1187002 reaction equation
[Na].[Br:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5](F)[C:4]=1[CH3:12].[CH3:13][OH:14]>>[Br:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([O:14][CH3:13])[C:4]=1[CH3:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545Sodium2×HCID 595569134-Bromo-2-fluoro-3-methylbenzonitrile

Product 1

HCID 666438674-Bromo-2-methoxy-3-methylbenzonitrile

Procedure

Sodium (3.00 g, 130 mmol) was added in portions into 80 mL of methanol and the mixture was stirred for 20 min until the sodium was completely dissolved. Then 4-bromo-2-fluoro-3-methylbenzonitrile (8.00 g, 37.3 mmol) was added and the solution was refluxed for 4 hours before cooling down. The reaction mixture was poured into ice/water (300 mL) and the resulting precipitate was collected by filtration. The solid afforded was dried under reduced pressure at 40° C. to give 4-bromo-3-methyl-2-(methyloxy)benzonitrile. 1H-NMR (400 MHz, CDCl3) δ ppm 7.39 (d, J=8.0 Hz, 1H), 7.28 (d, J=8.0 Hz, 1H), 4.00 (s, 3H), 2.37 (s, 3H).

Workup

  1. dissolutionwas completely dissolved
  2. temperaturethe solution was refluxed for 4 hours
  3. temperaturebefore cooling down
  4. filtrationthe resulting precipitate was collected by filtration
  5. customThe solid afforded
  6. customwas dried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-27acc3e8549448f8982dd8393ef75ba2
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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