Aluminum(III) Chloride → 2-Fluoro-4-(4-methyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-benzonitrile

HRID 469342Notes

Reaction equation

HRID 469342 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][C:4]=1[F:12])#[N:2].[CH3:13][C:14]1[C:19]2[NH:20][C:21](=[O:23])[O:22][C:18]=2[CH:17]=[CH:16][CH:15]=1.[Cl-].[Cl-].[Cl-].[Al+3]>>[F:12][C:4]1[CH:5]=[C:6]([C:7]([C:16]2[CH:15]=[C:14]([CH3:13])[C:19]3[NH:20][C:21](=[O:23])[O:22][C:18]=3[CH:17]=2)=[O:8])[CH:10]=[CH:11][C:3]=1[C:1]#[N:2]

Participants

4

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 127093364-Methyl-3H-benzooxazol-2-oneHCID 199567394-Cyano-3-fluorobenzoyl chloride

Product 1

HCID 581811882-Fluoro-4-(4-methyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-benzonitrile

Procedure

0.73 g (4.0 mmol) 4-cyano-3-fluoro-benzoic acid chloride, 0.60 g (4.0 mmol) 4-methyl-3H-benzoxazol-2-one and 2.1 g (16 mmol) aluminium trichloride were heated to 125° C. for 1.5 h with stirring. After cooling to RT the mixture was combined with ice water. The precipitate formed was suction filtered, washed with water and dried i. vac.

Workup

  1. customThe precipitate formed
  2. filtrationfiltered
  3. washwashed with water
  4. customdried i

Sources & evidence

ORD record
ord-844e169c07544f8e87ce02a2ab47f45d
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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