Ethanethiol → 3-Methoxy-4-(methylsulfanyl)phenol

The benzylether from stage (iii) (9.27 g, 39.5 mmol) was dissolved in DCM (5 mL), ethanethiol (5 mL) and BF3.OEt2 (5 mL, 39.5 mol) were then added at room temperature under a nitrogen atmosphere. The mixture was stirred overnight before the reaction was quenched with 2M HCl and stirred for a further 30 min. The mixture was then basified by the addition of 2M NaOH until pH 10 was attained. The mixture was then washed with EtOAc (3×50 mL). The aqueous layer was re-acidified by the addition of 2M HCl to pH 1 and extracted with EtOAc (4×50 mL). The extracts were combined, dried (MgSO4) and evaporated to an oil. Purification by flash chromatography [SiO2; EtOAc/pentane (1:9→1:4)] afforded the desired phenol compound as a colourless solid (1.73 g, 28%); δH (CDCl3, 400 MHz) 2.21 (3H, s), 3.70 (3H, s), 6.30 (1H, d), 6.35 (1H, s), 6.96 (1H, d), 9.39 (1H, brs).

1. customwas quenched with 2M HCl
2. stirringstirred for a further 30 min
3. additionThe mixture was then basified by the addition of 2M NaOH until pH 10
4. washThe mixture was then washed with EtOAc (3×50 mL)
5. additionThe aqueous layer was re-acidified by the addition of 2M HCl to pH 1
6. extractionextracted with EtOAc (4×50 mL)
7. dry with materialdried (MgSO4)
8. customevaporated to an oil
9. customPurification by flash chromatography [SiO2; EtOAc/pentane (1:9→1:4)]

ORD record

ord-06e630104681478e9148516800170974

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07129234B2