1-Bromopropane → 1-Iodo-4-propoxybenzene

HRID 625889ノート

反応式

HRID 625889 の反応式
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][CH3:12].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 78401-BromopropaneHCID 10340Sodium CarbonateHCID 108944-Iodophenol

生成物 1

HCID 132969221-Iodo-4-propoxybenzene収率 87%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A suspension of 4-iodophenol (3 g, 13.64 mmol), 1-bromopropane (1.845 g, 15.00 mmol), and sodium carbonate (7.54 g, 54.5 mmol) in DMF (30 mL) was stirred at 80° C. for 4 hrs. The reaction mixture was diluted with water (250 mL) and extracted with EtOAc (3×75 mL). The combined organic extracts were washed with 0.5M NaOH (2×50 mL), and water (2×50 mL), and then dried over MgSO4. The solvent was removed. The crude product (3.11 g) was obtained, which was directly used for the next reaction without further purification. 1H NMR (400 MHz, chloroform-d) δ 7.61-7.53 (m, 2H), 6.74-6.67 (m, 2H), 3.90 (t, J=6.5 Hz, 2H), 1.88-1.76 (m, 2H), 1.05 (t, J=7.4 Hz, 3H).

後処理

  1. extractionextracted with EtOAc (3×75 mL)
  2. washThe combined organic extracts were washed with 0.5M NaOH (2×50 mL), and water (2×50 mL)
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed

出典と根拠

ORDレコード
ord-366ce2d833d5422c8c97f48f5b992598
出典データセット
uspto-grants-2016_04
特許番号
US09308236B2

反応ノート

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