Reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[C:3]=1[C:4]#[N:5].ClC1C=CC=C(C(OO)=[O:27])C=1.S(=O)(O)[O-].[Na+]>O>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=[O:27])[C:3]=1[C:4]#[N:5]Participants
5
Procedure
To a solution of 2 g (7.7 mmol) of 2-fluoro-6-[(3-methoxyphenyl)thio]benzonitrile (Example 13) was added portionwise 1.6 g (9.3 mmol) of m-chloroperbenzoic acid. The resultant mixture was stirred for 24 h. Additional 0.16 g of m-chloroperbenzoic acid was added and the resultant mixture was stirred for 15 min. Excess sodium bisulfite was added, followed by water. The H2O solution was extracted with EtOAc. After drying over MgSO4 and solvent removal, the resultant crude product was purified by flash column chromatography on silica gel with methylene chloride as the eluent. This resulted in 1.7 g of 2-fluoro-6-[(3-methoxyphenyl)sulfinyl]benzonitrile as a solid: mp 103°-111° C.
Workup
- extractionThe H2O solution was extracted with EtOAc
- dry with materialAfter drying over MgSO4 and solvent removal
- customthe resultant crude product was purified by flash column chromatography on silica gel with methylene chloride as the eluent
- customThis resulted in 1.7 g of 2-fluoro-6-[(3-methoxyphenyl)sulfinyl]benzonitrile as a solid
Sources & evidence
- ORD record
- ord-f52f628e55bf48349560d5f7350120df
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05723452
Linked notes
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