Benzyl Chloride → 4-Benzyloxy-3-chloroaniline

To 4-amino-2-chlorophenol (17.24 g, 50 mmol) dissolved in acetone (250 mL) was added potassium carbonate (6.93 g, 50 mmol) followed by addition of benzyl chloride (5.8 mL, 50 mmol), TBAB (1.64 g, 50 mmol) and potassium hydroxide (2.83 g, 5 mmol). The reaction mixture is allowed to stir at reflux overnight under nitrogen. The reaction mixture was filtered and extracted 3 times with dichloromethane. The combined organic layers were washed two times with 10% NaOH, washed one time with brine, dried over potassium carbonate and then filtered. The sample was concentrated on the rotary evaporator and the resulting oil was dried overnight under vacuum. Flash column chromatography (SiO2, 50:50 hexanes:ethyl acetate) yielded a dark brown oil (160a, 7.3 g, 62%); HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 14.6 min, 97.7% purity; MS (TOF MS ES+): m/z 275 (M+CH3CN+H, 100), 234 (M+H, 11.8).

1. temperatureat reflux overnight under nitrogen
2. filtrationThe reaction mixture was filtered
3. extractionextracted 3 times with dichloromethane
4. washThe combined organic layers were washed two times with 10% NaOH
5. washwashed one time with brine
6. dry with materialdried over potassium carbonate
7. filtrationfiltered
8. concentrationThe sample was concentrated on the rotary evaporator
9. customthe resulting oil was dried overnight under vacuum

ORD record

ord-513d02ecbc2844c1ac0df3137c9a9f17

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07335770B2