Ethyl Thioglycolate → Ethyl 6-bromo-1-benzothiophene-2-carboxylate

HRID 250264

反応式

HRID 250264 の反応式
[H-].[Na+].[SH:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[C:13](F)[CH:12]=1>CS(C)=O>[CH2:8]([O:7][C:5]([C:4]1[S:3][C:13]2[CH:12]=[C:11]([Br:10])[CH:18]=[CH:17][C:14]=2[CH:15]=1)=[O:6])[CH3:9]

参加物

5

反応物 3

HCID 12185Ethyl ThioglycolateHCID 24758Sodium hydrideHCID 1435174-Bromo-2-fluorobenzaldehyde

生成物 1

HCID 13567982Ethyl 6-bromo-1-benzothiophene-2-carboxylate収率 86%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Sodium hydride (1.41 g, 35.32 mmol) is added to a round bottom flask and washed with hexanes (10 mL) twice. To the flask is added dimethyl sulfoxide (30 mL) and ethyl 2-mercaptoacetate (3.54 g, 29.43 mmol). The mixture is stirred for 10 minutes and 4-bromo-2-fluoro-benzaldehyde (4.78 g; 23.55 mmol) is added. The reaction mixture is stirred for 15 minutes and quenched with ice-water (100 g). The mixture is extracted with CH2Cl2 (50 mL×2). The combined organic layers are dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product is purified via flash chromatography eluting with 10% EtOAc/Hexanes. The appropriate fractions are combined and concentrated under reduced pressure to afford the title compound (5.75 g, 86%). 1H NMR (400 MHz, CDCl3): δ 8.00 (s, 1H), 7.99 (s, 1H), 7.75 (d, 1H), 7.48 (d, 1H), 4.38 (q, 2H), 1.39 (t, 3H).

後処理

  1. washwashed with hexanes (10 mL) twice
  2. stirringThe reaction mixture is stirred for 15 minutes
  3. customquenched with ice-water (100 g)
  4. extractionThe mixture is extracted with CH2Cl2 (50 mL×2)
  5. dry with materialThe combined organic layers are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product is purified via flash chromatography
  9. washeluting with 10% EtOAc/Hexanes
  10. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-ab7dca92f13d4b9a957f4b24ffc6ac5a
出典データセット
uspto-grants-2011_01
特許番号
US07863302B2

関連ノート

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