Methanol → 2-(Isopropylthio)benzaldehyde

To a solution of 2-(isopropylthio)benzoic acid (0.98 g, 5 mmol) in THF (10 ml) was added dropwise borane-dimethyl sulphide complex (0.8 ml, 8 mmol) at 3° C. under argon with vigorous stirring. After continuing to stir in an ice bath for 30 min, the reaction was left to stand at RT for a further 24 h. Methanol (1.5 ml) was added cautiously and the reaction solution was concentrated under reduced pressure. The residue was taken up in diethyl ether (50 ml), and washed with saturated K2CO3 solution and NaCl solution. Aqueous solutions were additionally extracted with ether, the combined organic phases were dried over MgSO4 and filtered, and the solvent was removed under reduced pressure. The residue was taken up in dichloromethane (30 ml), admixed cautiously with PCC (1.20 g, 5.6 mmol) and stirred at room temperature for 36 h. After solvent removal, the residue was purified by column chromatography on silica gel (10:1 hexane:ethyl acetate). Yield 0.69 g (76%).

1. waitthe reaction was left
2. waitto stand at RT for a further 24 h
3. concentrationthe reaction solution was concentrated under reduced pressure
4. washwashed with saturated K2CO3 solution and NaCl solution
5. extractionAqueous solutions were additionally extracted with ether
6. dry with materialthe combined organic phases were dried over MgSO4
7. filtrationfiltered
8. customthe solvent was removed under reduced pressure
9. stirringstirred at room temperature for 36 h
10. customAfter solvent removal
11. customthe residue was purified by column chromatography on silica gel (10:1 hexane:ethyl acetate)

ORD record

ord-2e00666dd36549beaeae3c324bb907de

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08183382B2