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

HRID 1482678ノート

反応式

HRID 1482678 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 694127502-(Benzyloxy)-1-fluoro-4-nitrobenzene収率 84.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
50 °C

実験手順

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).

後処理

  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.

出典と根拠

ORDレコード
ord-66bcb0e65d6f43b9869941c81b95a463
出典データセット
uspto-grants-2016_08
特許番号
US09415049B2

反応ノート

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