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

HRID 1909519노트

반응식

HRID 1909519 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 126239032-Methyl-1-benzothiophene-7-carboxylic acid수율 31.2%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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]−.

후처리

  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

출처 및 근거

ORD 기록
ord-f3339f28b72d496fb6a0334c0c657429
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598374B2

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