4-Fluoro-3-methylbenzamide → 4-Fluoro-3-methylbenzonitrile

HRID 2094247Notes

Reaction equation

HRID 2094247 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=O)=[CH:4][C:3]=1[CH3:11]>P(Cl)(Cl)(Cl)=O>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]#[N:8])=[CH:4][C:3]=1[CH3:11]

Participants

3

Reactant 1

HCID 27745784-Fluoro-3-methylbenzamide

Product 1

HCID 27791804-Fluoro-3-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

10.00 g (65.29 mmol) 4-fluoro-3-methyl-benzoic acid amide are stirred together with 50 ml phosphorus oxychloride for 4 hours at 60° C. and then evaporated down i. vac. The residue is poured into ice water, the resulting precipitate is filtered off and washed with water. After being taken up in ethyl acetate the organic phase is washed with sat. potassium carbonate solution, dried over sodium sulphate and evaporated down completely i. vac.

Workup

  1. customevaporated down i
  2. additionThe residue is poured into ice water
  3. filtrationthe resulting precipitate is filtered off
  4. washwashed with water
  5. washis washed with sat. potassium carbonate solution
  6. dry with materialdried over sodium sulphate
  7. customevaporated down completely i

Sources & evidence

ORD record
ord-d1ecfa7c32d0403b8bc3541283961648
Source dataset
uspto-grants-2013_05
Patent number
US08445525B2

Reaction notes

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