1-Bromo-2-Chloroethane → 1-(2-chloroethoxy)-3-nitrobenzene

HRID 1157550ノート

反応式

HRID 1157550 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:18][CH2:19][Cl:20]>CC(=O)CC.CCOC(C)=O.O>[N+:1]([C:4]1[CH:5]=[C:6]([O:10][CH2:18][CH2:19][Cl:20])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

参加物

7

反応物 3

HCID 78491-Bromo-2-ChloroethaneHCID 111373-NitrophenolHCID 11430Potassium Carbonate

生成物 1

HCID 43044241-(2-chloroethoxy)-3-nitrobenzene収率 58.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6569Methyl Ethyl Ketone溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of 3-nitrophenol (5.0 g, 36 mmol) and K2CO3 (7.45 g, 54 mmol), in 2-butanone at 85° C. was added 1-bromo-2-chloroethane (1.7 mL, 71.9 mmol) and the reaction stirred for 24 h. The mixture was cooled to rt and reduced in vacuo. The crude was diluted with EtOAc (200 mL) and water (200 mL) and separated. The aqueous layer was extracted twice with EtOAc (200 mL), the organics were pooled, dried over MgSO4 and reduced in vacuo onto silica gel. Purification was achieved via column chromatography using a gradient of EtOAc/Hexanes to afford a yellow oil that solidified upon standing to afford 4.22 g (58% yield) of titled product as an off-white solid. 1H NMR (400 MHz, DMSO-D6) δ ppm 7.8 (m, 1H), 7.7 (t, J=2.4 Hz, 1H), 7.6 (t, J=8.2 Hz, 1H) 7.4 (dd, J=8.2, 2.6 Hz, 1H), 4.4 (m, 2H), 4.0 (m, 2H).

後処理

  1. customseparated
  2. extractionThe aqueous layer was extracted twice with EtOAc (200 mL)
  3. dry with materialdried over MgSO4
  4. customPurification
  5. customto afford a yellow oil

出典と根拠

ORDレコード
ord-bb9b5332ebbe4046b919c81eeaaaf7fe
出典データセット
uspto-grants-2010_10
特許番号
US07807673B2

反応ノート

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