3-Fluorophenol → Nitro-4-(3-fluoro-phenoxymethyl)-benzene

HRID 1827385노트

반응식

HRID 1827385 반응식
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:31][C:32]1[CH:33]=[C:34](O)[CH:35]=[CH:36][CH:37]=1>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:36]2[CH:35]=[CH:34][CH:33]=[C:32]([F:31])[CH:37]=2)=[CH:10][CH:11]=1)([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 97433-FluorophenolHCID 11776TriphenylphosphineHCID 692754-Nitrobenzyl alcohol

생성물 1

HCID 22137955Nitro-4-(3-fluoro-phenoxymethyl)-benzene수율 78.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2.0 g (13 mmol) 4-nitrobenzyl alcohol and 3.60 g (13.7 mmol) triphenylphosphine in 30 ml tetrahydrofurane is treated with 1.54 g (13.7 mmol) of 3-fluorophenol. The mixture is cooled in an ice-bath and 2.39 g (13.7 mmol) of diethyl-aza-dicarboxylate is slowly added. The ice-bath is removed and the reaction mixture stirred over night at room temperature. The tetrahydrofuran is evaporated, the oily residue triturated with diethyl ether, filtered and concentrated. Chromatography (silica gel, ethyl acetate/hexane 1:9) yields 2.52 g (78%) of the title compound as a slightly yellow solid. MS: m/e=247.1 (M++H).

후처리

  1. temperatureThe mixture is cooled in an ice-bath
  2. customThe ice-bath is removed
  3. customThe tetrahydrofuran is evaporated
  4. customthe oily residue triturated with diethyl ether
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ec75381d77b74dd780f41346afa305e6
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07053245B2

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