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

HRID 1827385ノート

反応式

HRID 1827385 の反応式
[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]

参加物

5

反応物 3

HCID 97433-FluorophenolHCID 11776TriphenylphosphineHCID 692754-Nitrobenzyl alcohol

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ec75381d77b74dd780f41346afa305e6
出典データセット
uspto-grants-2006_05
特許番号
US07053245B2

反応ノート

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