Bromine → HCID 16733861, compound

Temperature

70 °C

In a 100 mL 2-neck round-bottomed flask 2-(methylthio)benzaldehyde (5 grams, 32.8 mmol) and iron(III) bromide (0.485 grams, 1.642 mmol) were dissolved in PhCl (10 ml) to give a brown solution. The reaction mixture was heated to 70° C. and treated dropwise with a solution of bromine (1.78 mL, 34.5 mmol) in PhCl (8 mL) via an addition funnel. The mixture was heated at 70° C. After 5 hours, the heating source was removed and the reaction was cooled to room temperature. The reaction mixture was quenched with a 1:1 mixture of aqueous saturated NaHCO3/Na2SO3 solution (30 mL total). The aqueous layer was separated and extracted with CH2Cl2 (50 mL). The combined organic layers were dried (MgSO4), filtered and concentrated using a rotary evaporator. The residual solution was cooled in the freezer overnight. The crude product precipitated and was isolated by decanting the excess PhCl and drying the product under high vacuum overnight. The structure was confirmed by 1H and 13C NMR spectroscopy. Yield 4.5 grams (60%).

1. customto give a brown solution
2. temperatureThe mixture was heated at 70° C
3. customthe heating source was removed
4. temperaturethe reaction was cooled to room temperature
5. customThe reaction mixture was quenched with a 1:1 mixture of aqueous saturated NaHCO3/Na2SO3 solution (30 mL total)
6. customThe aqueous layer was separated
7. extractionextracted with CH2Cl2 (50 mL)
8. dry with materialThe combined organic layers were dried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customa rotary evaporator
12. temperatureThe residual solution was cooled in the freezer overnight
13. customThe crude product precipitated
14. customwas isolated
15. customby decanting the excess PhCl
16. customdrying the product under high vacuum overnight

ORD record

ord-87fdea2028d346b7b91d4c399d070df8

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08283660B2