Carbon Dioxide → 3-Chloro-5-cyclopropylbenzoic acid

HRID 19804ノート

反応式

HRID 19804 の反応式
Br[C:2]1[CH:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[CH:5]=[C:4]([Cl:11])[CH:3]=1.[Li]CCCC.[C:17](=[O:19])=[O:18]>C1COCC1>[Cl:11][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[CH:5]=1)[C:17]([OH:19])=[O:18]

参加物

5

反応物 3

HCID 280Carbon DioxideHCID 665209601-Bromo-3-chloro-5-cyclopropylbenzeneHCID 178418339Butyllithium

生成物 1

HCID 685583713-Chloro-5-cyclopropylbenzoic acid収率 70%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-bromo-3-chloro-5-cyclopropylbenzene (300 mg, 1.30 mmol) at −78° C. in THF (5 ml) was added nBuLi (890 μl, 1.6M solution in hexane, 1.43 mmol) dropwise. The resulting solution was stirred at −78° C. for 10 min after which solid carbon dioxide was added and the reaction mixture was warmed to RT over 3 hours. The reaction mixture was quenched with water and then extracted with ether. The aqueous phase was then made acidic with 1N HCl and then extracted with ethyl acetate. The organic phases were combined, washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give the desired product 3-chloro-5-cyclopropylbenzoic acid (178 mg, 70%) which did not require further purification. MS (ISP) 195.1 (M−H)−.

後処理

  1. additionwas added
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ether
  4. extractionmade acidic with 1N HCl and then extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0e51a125eab742b29af011c56a4f3d66
出典データセット
uspto-grants-2010_06
特許番号
US07745477B2

反応ノート

読み込み中…