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

HRID 1159938ノート

反応式

HRID 1159938 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 58.2%

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, 35.94 mmol), K2CO3 (7.45 g, 53.9 mmol), in 2-butanone at 85° C. 1-bromo-2-chloroethane (1.723 mL, 71.88 mmol) was added and stirred for 24 h. The mixture was cooled to rt and reduced in vacuo, then diluted with EtOAc (200 mL) and water (200 mL) and separated. The aqueous layer was extracted twice with EtOAc (200 mL) and the combined organic layers were dried over MgSO4 and reduced in vacuo onto silica. Purified via column chromatography using gradient of EtOAc/Hexanes to afford a yellow oil that solidified upon standing to afford 4.22 g (58% yield) of desired product as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 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. customat 85° C
  2. customseparated
  3. extractionThe aqueous layer was extracted twice with EtOAc (200 mL)
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. customPurified via column chromatography
  6. customto afford a yellow oil

出典と根拠

ORDレコード
ord-00bbdbb609644558964ac929e2719a81
出典データセット
uspto-grants-2010_10
特許番号
US07812022B2

反応ノート

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