Benzyl Bromide → 2-(Benzyloxy)-1-fluoro-4-nitrobenzene

HRID 2274261노트

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HRID 2274261 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCCCCC.C(OCC)(=O)C>CN(C=O)C.O>[CH2:18]([O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[F:1])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

7

반응물 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 234981002-Fluoro-5-nitrophenol

생성물 1

HCID 694127502-(Benzyloxy)-1-fluoro-4-nitrobenzene수율 84.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

반응 조건

온도
50 °C

실험 절차

In a 50 mL 3-neck RBF equipped with reflux condenser, magnetic stirrer and thermo pocket were charged 2-fluoro-5-nitrophenol (2.4 g), K2CO3 (3.16 g) and dry DMF (20 mL). The reaction mixture was heated at 50° C. for 30 min. followed by addition of benzyl bromide (2.87 g) in DMF and the reaction mixture was heated to 80° C. for 18 hr. The reaction was monitored on TLC using hexane:ethyl acetate (5:5) as mobile phase. The reaction was complete after 30 minutes. After completion, the reaction mixture was poured into cold water. The solid precipitate was filtered and washed with water and dried under reduced pressure at 45° C. to give 3.20 g of 2-(benzyloxy)-1-fluoro-4-nitrobenzene. 1H NMR: DMSO-d6 (400 MHz): 5.35 (s, 2H), 7.358-7.397 (m, 1H), 7.415-7.454 (m, 2H), 7.448-7.530 (m, 2H), 7.553-7.579 (m, 1H), 7.900-7.939 (m, 1H), 8.091-8.116 (dd, 1H, J=2.8, 4.4).

후처리

  1. customIn a 50 mL 3-neck RBF equipped
  2. temperaturewith reflux condenser, magnetic stirrer
  3. temperaturethe reaction mixture was heated to 80° C. for 18 hr
  4. filtrationThe solid precipitate was filtered
  5. washwashed with water
  6. customdried under reduced pressure at 45° C.

출처 및 근거

ORD 기록
ord-62d3266f1599438499b5228bc6cc4022
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126950B2

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