Carbon Dioxide → 5-Chloro-2-fluoro-4-methylbenzoic acid

HRID 1427906ノート

反応式

HRID 1427906 の反応式
Br[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([CH3:9])=[CH:4][C:3]=1[F:10].C([Mg]Cl)(C)C.[C:16](=[O:18])=[O:17]>C1COCC1>[Cl:8][C:6]1[C:5]([CH3:9])=[CH:4][C:3]([F:10])=[C:2]([CH:7]=1)[C:16]([OH:18])=[O:17]

参加物

5

反応物 3

HCID 280Carbon DioxideHCID 27362284-Bromo-2-chloro-5-fluorotolueneHCID 178418918HCID 178418918、化合物

生成物 1

HCID 580424465-Chloro-2-fluoro-4-methylbenzoic acid収率 49%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-bromo-5-chloro-2-fluoro-4-methylbenzene (11.3 g, 50 mmol) in dry THF (100 mL) was added isopropylmagnesium chloride (30 mL, 2 M) dropwise. After stirring at room temperature for 30 min, dry CO2 was added and the mixture was stirred at room temperature for additional 30 min. The reaction was quenched by sat. NH4Cl and extracted with EtOAc (100 mL×3). The combined organic layers were washed with water (50 mL×3), dried over anhydrous Na2SO4, filtered and concentrated to give the desired product (4.7 g, 49%). LCMS (ESI) m/z: 187.0 [M−H]−.

後処理

  1. stirringthe mixture was stirred at room temperature for additional 30 min
  2. customThe reaction was quenched by sat. NH4Cl
  3. extractionextracted with EtOAc (100 mL×3)
  4. washThe combined organic layers were washed with water (50 mL×3)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-c8e479a946ac4461b7c6b48f58814573
出典データセット
uspto-grants-2015_01
特許番号
US08933236B2

反応ノート

読み込み中…