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

HRID 2069607ノート

反応式

HRID 2069607 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-ec5f0e6ef3524ddeb5934f2d83b98782
出典データセット
uspto-grants-2012_10
特許番号
US08299117B2

反応ノート

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