Trifluoroacetic acid → 2-Chloro-6-hydroxybenzonitrile

HRID 650106Notes

Reaction equation

HRID 650106 reaction equation
C([C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:10]=1[C:11]#[N:12])(=O)C1C=CC=CC=1.FC(F)(F)C(O)=[O:21]>C(Cl)Cl>[C:11]([C:10]1[C:13]([Cl:17])=[CH:14][CH:15]=[CH:16][C:9]=1[OH:21])#[N:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21714411HCID 21714411, compound

Product 1

HCID 44079952-Chloro-6-hydroxybenzonitrileYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Benzoyl-6-chlorobenzonitrile (10.0 g, 41 mmol) was dissolved in methylene chloride(40 ml) and trifluoroacetic acid(40 ml) and stirred at room temperature for 24 hrs. The reaction mixture is diluted with methylene chloride and extracted with water. The organic layer is dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4%MeOH/CHCl2) gave the desired product(4.2 g, 67%). 1H NMR (CD3COCD3): δ10.31 (s,1H), 7.51 (t, 1H), 7.11 (d, 1H) 7.05 (d, 1H).

Workup

  1. extractionextracted with water
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-6f65d7e8ef73451699026d5d6ab266c5
Source dataset
uspto-grants-2001_08
Patent number
US06271261B1

Reaction notes

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