Ethanol → Ethyl 6-bromonaphthalene-2-carboxylate

HRID 324225

反応式

HRID 324225 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.[CH2:15](O)[CH3:16].S(=O)(=O)(O)O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:5]2

参加物

4

反応物 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 45498526-Bromo-2-naphthalenecarboxylic acid2 回

生成物 1

HCID 1249959Ethyl 6-bromonaphthalene-2-carboxylate

実験手順

To a solution of 6-bromo-2-naphthalenecarboxylic acid (Compound M) 3.1 g, (12.43 mmol) in ethanol (30 ml, 23.55 g, 511.0 mmol) was added 18M sulfuric acid (2 ml). The solution was Tefluxed for 30 minutes, cooled to room temperature, and the reaction mixture partitioned between pentane (100 ml) and water (100 ml). The aqueous phase was extracted with pentane (100 ml) and the combined organic layers washed with saturated aqueous NaCl (100 ml), dried MgSO4), and concentrated to yield an off-white solid. Purification by flash chromatography (silica, 10% EtOAc-hexane) afforded the title compound as a white solid. 1H NMR (CDCl3): δ 8.58 (1H, br s), 8.10 (1H, dd, J=1.7, 9 Hz), 8.06 (1H, d, J=2 Hz), 7.83 (1H, d, J=9 Hz), 7.80 (1H, d, J=9 Hz), 7.62 (1H, dd, J=2, 9 Hz).

後処理

  1. customfor 30 minutes
  2. customthe reaction mixture partitioned between pentane (100 ml) and water (100 ml)
  3. extractionThe aqueous phase was extracted with pentane (100 ml)
  4. washthe combined organic layers washed with saturated aqueous NaCl (100 ml), dried MgSO4), and
  5. concentrationconcentrated
  6. customto yield an off-white solid
  7. customPurification by flash chromatography (silica, 10% EtOAc-hexane)

出典と根拠

ORDレコード
ord-7f7a5872e19d461387095ee136dc3a75
出典データセット
uspto-grants-2001_04
特許番号
US06218128B1

関連ノート

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