반응 #1261973

반응 방정식

H2O

1-benzyloxy-4-(2-bromo-ethyl)-2-fluoro-benzene

morpholine

K2CO3

→

desired compound

수율 109.6%

2-fluoro-4-(2-morpholin-4-yl-ethyl)-phenol

수율 109.6%

용매

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONadded
2. 2
   온도maintained for 6 hours
3. 3
   온도The reaction was cooled to room temperature
4. 4
   추출The organic compound was extracted with ethyl acetate (50 mL)
5. 5
   건조dried over MgSO4
6. 6
   농축The ethyl acetate layer was concentrated under vacuum
7. 7
   workup.DISSOLUTIONdissolved in methanol (50 mL)
8. 8
   workup.ADDITIONThe solution was treated with Pd/C (20 mg)
9. 9
   여과The solid material was filtrated off
10. 10
    농축the filtrate was concentrated under vacuum

실험 절차

To a solution of 1-benzyloxy-4-(2-bromo-ethyl)-2-fluoro-benzene (1.0 g, 3.2 mmol) and morpholine (278 mg, 3.2 mmol) in DMF (5 mL), was K2CO3 (432 mg, 3.2 mmol) added. The reaction mixture was heated to 60° C. and maintained for 6 hours. The reaction was cooled to room temperature and poured into H2O (50 mL). The organic compound was extracted with ethyl acetate (50 mL) and dried over MgSO4. The ethyl acetate layer was concentrated under vacuum and dissolved in methanol (50 mL). The solution was treated with Pd/C (20 mg) and stirred under H2 (1 atm) for 3 hours. The solid material was filtrated off and the filtrate was concentrated under vacuum to afford the desired compound (790 mg, 93%) as a white oil. The crude compound was used for the next step without further purification. 1H NMR (400 Mz, DMSO-d6) δ 7.33-7.45 (m, SH), 7.09-7.15 (m, 2H), 6.97-7.01 (m, 1H), 5.13 (s, 2H), 3.56 (m, 4H), 2.64-2.68 (m, 2H), 2.44-2.50 (m, 2H), 2.39 (b, 2H). LCMS 310.5 [MH+].

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