Sodium Iodide → Hydroxybupropion

2-Amino-1-methyl-propan-1-ol (14 ml, 0.15 mol) was added to α-bromo-3′chloro propiophenone (18 g, 73 mmol) in suspension in chloroform (50 ml), with two crystals of sodium iodide. The reaction was heated under reflux overnight. After filtration the organic phase was extracted twice with a 2M HCl solution (2×100 ml). The aqueous phase wash washed with DCM then neutralised with sodium carbonate. The aqueous layer was extracted with DCM. The organic phase was dried over magnesium sulphate, filtered and evaporated. Recrystallisation from chloroform gives the desired compound in 55% yield as a white solid (10.2 g, 40 mmol).

1. temperatureThe reaction was heated
2. temperatureunder reflux overnight
3. filtrationAfter filtration the organic phase
4. extractionwas extracted twice with a 2M HCl solution (2×100 ml)
5. washThe aqueous phase wash
6. washwashed with DCM
7. extractionThe aqueous layer was extracted with DCM
8. dry with materialThe organic phase was dried over magnesium sulphate
9. filtrationfiltered
10. customevaporated
11. customRecrystallisation from chloroform

ORD record

ord-cd904f3fb37b4f26aa8a124b8bcf2937

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188150B2