1,2-Dibromoethane → 7-Fluoro-5-nitro-2,3-dihydrobenzo[b][1,4]dioxine

HRID 1054444노트

반응식

HRID 1054444 반응식
C([O-])([O-])=O.[K+].[K+].[F:7][C:8]1[CH:13]=[C:12]([OH:14])[C:11]([OH:15])=[C:10]([N+:16]([O-:18])=[O:17])[CH:9]=1.Br[CH2:20][CH2:21]Br>CN(C=O)C.C(OCC)(=O)C>[F:7][C:8]1[CH:9]=[C:10]([N+:16]([O-:18])=[O:17])[C:11]2[O:15][CH2:21][CH2:20][O:14][C:12]=2[CH:13]=1

참가 물질

6

반응물 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 688163705-Fluoro-3-nitrobenzene-1,2-diol

생성물 1

HCID 688171507-Fluoro-5-nitro-2,3-dihydrobenzo[b][1,4]dioxine수율 99%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

K2CO3 (15.27 g, 110.6 mmol) was added to a solution of 5-fluoro-3-nitrobenzene-1,2-diol (5 g, 28.9 mmol) in DMF (35 mL) followed by the addition of 1,2-Dibromoethane (13.63 g, 6.25 mL, 72.5 mmol) and stirring was continued at 80° C. for 2 h. Reaction mixture was diluted with ethyl acetate, washed with cold water, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the crude, which was purified by MPLC (silica gel, Mobile Phase: ethyl acetate in n-Hexane 0 to 5% as eluant) to afford 7-fluoro-5-nitro-2,3-dihydrobenzo[b][1,4]dioxine (Int-26) (5.7 g, 85% yield) as pale yellow solid. 1H NMR (300 MHz, CDCl3) δ 7.3-7.2 (1H, dd), 6.9-6.8 (1H, dd), 4.4 (4H, s) ppm.

후처리

  1. customReaction mixture
  2. washwashed with cold water
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude, which
  6. customwas purified by MPLC (silica gel, Mobile Phase: ethyl acetate in n-Hexane 0 to 5% as eluant)

출처 및 근거

ORD 기록
ord-ecd71a84c7fe4fe9aa8a3f60bc7be679
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394305B2

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