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

HRID 500656

反応式

HRID 500656 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.O>CS(C)=O>[Br:10][C:11]1[CH:18]=[CH:17][C:14]2[CH:15]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[S:3][C:13]=2[CH:12]=1

参加物

6

反応物 4

HCID 962WaterHCID 12185Ethyl ThioglycolateHCID 24758Sodium hydrideHCID 1435174-Bromo-2-fluorobenzaldehyde

生成物 1

HCID 13567982Ethyl 6-bromo-1-benzothiophene-2-carboxylate収率 44%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

Sodium hydride (60% dispersion in mineral oil, 0.73 g, 18.3 mmol) was suspended in DMSO (10 mL) and ethyl mercaptoacetate (1.111 mL, 10.1 mmol) was added potionwise using a water bath to moderate the exotherm. On complete addition, the water bath was removed and stirring continued for 15 minutes. A solution of 4-bromo-2-fluorobenzaldehyde (1.86 g, 9.16 mmol) in DMSO (2 mL) was added in one portion. The dark solution was stirred for 15 minutes before pouring into cold water (300 mL). The products were extracted into Et2O (2×200 mL). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by MPLC gave 1.15 g of desired product (pale yellow solid, 44%). 1H NMR (DMSO-d6) δ 8.37 (d, J=1.8 Hz, 1H), 8.17 (s, 1H), 7.94 (d, J=8.4 Hz, 1H), 7.60 (dd, J=8.4, 1.8 Hz, 1H), 4.32 (q, J=7.2 Hz, 2H), 1.30 (t, J=7.2 Hz, 3H).

後処理

  1. additionOn complete addition
  2. customthe water bath was removed
  3. stirringThe dark solution was stirred for 15 minutes
  4. extractionThe products were extracted into Et2O (2×200 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by MPLC

出典と根拠

ORDレコード
ord-1f8dec0ddc78408580c916a463a8ce46
出典データセット
uspto-grants-2010_08
特許番号
US07772238B2

関連ノート

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