Carbon Dioxide → 2-Methyl-1-benzothiophene-7-carboxylic acid

HRID 1876362ノート

反応式

HRID 1876362 の反応式
Br[C:2]1[C:7]2[S:8][C:9]([CH3:11])=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:17](=[O:19])=[O:18]>O1CCCC1.C(OCC)C>[CH3:11][C:9]1[S:8][C:7]2[C:2]([C:17]([OH:19])=[O:18])=[CH:3][CH:4]=[CH:5][C:6]=2[CH:10]=1

参加物

6

反応物 3

HCID 280Carbon DioxideHCID 126238737-Bromo-2-methyl-1-benzothiopheneHCID 178418339Butyllithium

生成物 1

HCID 126239032-Methyl-1-benzothiophene-7-carboxylic acid収率 31.2%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

The solution of 7-bromo-2-methylbenzo[b]thiophene (508) (0.908 g, 4.0 mmol) in tetrahydrofuran (16 mL) was cooled to −78° C. under nitrogen. n-butyllithium (2.40 mL, 6.0 mmol, 1.0M in Hexanes) was added dropwise. After the addition was complete, the reaction mixture was stirred at −78° C. for 1 h, then poured on to the mixture of dry ice in ethyl ether (30 mL). The reaction was stirred to reach room temperature for 5 hours, followed by washing with 1N HCl, brine and dried over sodium sulfate, filtered, and concentrated in vacuo. The obtained white solid was washed with hexanes to provide 2-methylbenzo[b]thiophene-7-carboxylic acid (509) (0.240 g, 31.2%). LC-MS ESI m/z: found 191.0 [M−H]−.

後処理

  1. additionAfter the addition
  2. stirringThe reaction was stirred
  3. waitto reach room temperature for 5 hours
  4. washby washing with 1N HCl, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. washThe obtained white solid was washed with hexanes

出典と根拠

ORDレコード
ord-f9b0d2dfb2e840bf8612157110decb21
出典データセット
uspto-grants-2012_11
特許番号
US08309600B2

反応ノート

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