Water → 3-(Methylsulfanyl)phenol

1-Methoxy-3-methylsulfanyl-benzene (32.87 g, 0.213 mol) was dissolved in a mixture of 30% hydrogen bromide in acetic acid (96 ml) and 48% aqueous hydrobromic acid (24 ml). The reaction was heated to reflux, and stirred at this temperature under nitrogen for 5.5 h. After cooling to room temperature the reaction mixture was poured into water (600 ml) and extracted with diethylether (3×300 ml). The combined organic extracts were washed with water (2×150 ml), brine (100 ml), dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with a solvent gradient of ethyl acetate:pentane (1:19 changing to 3:37 then 1:9, by volume) and the product was azeotroped with toluene (2×100 ml) to give 3-Methylsulfanyl-phenol (19.3 g) as a crimson oil.

1. temperatureThe reaction was heated
2. temperatureto reflux
3. extractionextracted with diethylether (3×300 ml)
4. washThe combined organic extracts were washed with water (2×150 ml), brine (100 ml)
5. dry with materialdried over MgSO4
6. customthe solvent was removed under reduced pressure
7. customThe residue was purified by flash column chromatography on silica gel eluting with a solvent gradient of ethyl acetate:pentane (1:19 changing to 3:37
8. custom1:9, by volume) and the product was azeotroped with toluene (2×100 ml)

ORDレコード

ord-08f220e713054f1cb719e2ba1fd56a56

出典データセット

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07141586B2