2-Bromopropane → HCID 86723246, compound

To a solution of 4-bromo-3-fluorobenzene-1-sulfonyl chloride (5.40 mL, 36.5 mmol) in THF (150 mL) at 0° C. was added hydrazine monohydrate (6.20 mL, 63.9 mmol) dropwise under a nitrogen atmosphere. The reaction mixture was stirred for 1.5 hours. The solvent was removed in vacuo and replaced with heptanes (150 mL) and the resulting precipitate was collected by filtration. The solid was dissolved in industrial methylated spirit (150 mL) and to this solution was added sodium acetate (17.9 g, 218 mmol) and 2-bromopropane (17.2 mL, 183 mmol). The resultant reaction mixture was stirred at 85° C. for 16 hours under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and quenched with water (300 mL) before being extracted with CH2Cl2 (3×300 mL). The combined organic extracts were washed with brine (300 mL), dried over MgSO4, filtered and evaporated in vacuo. The crude material was purified by silica gel column chromatography eluting with EtOAc:heptanes 20/80 to afford title compound as a colourless solid in 12% yield, 1.19 g.

1. customThe solvent was removed in vacuo
2. filtrationthe resulting precipitate was collected by filtration
3. dissolutionThe solid was dissolved in industrial methylated spirit (150 mL) and to this solution
4. customThe resultant reaction mixture
5. stirringwas stirred at 85° C. for 16 hours under a nitrogen atmosphere
6. customquenched with water (300 mL)
7. extractionbefore being extracted with CH2Cl2 (3×300 mL)
8. washThe combined organic extracts were washed with brine (300 mL)
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. customevaporated in vacuo
12. customThe crude material was purified by silica gel column chromatography
13. washeluting with EtOAc

ORD record

ord-04e602a484734e43a5a012eca7081169

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952008B2