Ethanethiol → 2-broMo-5-hydroxybenzoic acid Methyl ester

To a cold solution (ice water bath) of the methyl-2-bromo-5-methoxybenzoate (2.00 g, 8.16 mmol) in dichloromethane (15 mL) was added AlCl3(5.44 g, 40.8 mmol) under argon, and the reaction temperature was maintained below 10° C. using an ice-water bath. The light brown suspension was stirred for 10 min, then EtSH (3.02 mL, 40.8 mmol) was added dropwise at such a rate that the reaction temperature was maintained below 5° C. After 2.5 h of stirring below 10° C., the reaction mixture was slowly poured into ice water with agitation. The organic layer was separated, and the aqueous layer was extracted with DCM. The combined organic layers were washed with water, dried over MgSO4, filtered and concentrated under reduced pressure to afford a light yellow oil which was used in the next step without further purification.

1. temperaturethe reaction temperature was maintained below 10° C.
2. temperaturewas maintained below 5° C
3. stirringAfter 2.5 h of stirring below 10° C.
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted with DCM
6. washThe combined organic layers were washed with water
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customto afford a light yellow oil which
11. customwas used in the next step without further purification

ORD record

ord-eef416e2c4354f72b0c5557203562434

Source dataset

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07265144B2