Dichloromethane → Ethyl 2-chloro-5-cyclopropylbenzoate

HRID 41999

反応式

HRID 41999 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:13])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH:14]1(B2OC(C)(C)C(C)(C)O2)[CH2:16][CH2:15]1.C([O-])([O-])=O.[Cs+].[Cs+].C(Cl)Cl>O1CCOCC1.O>[Cl:13][C:5]1[CH:4]=[CH:3][C:2]([CH:14]2[CH2:16][CH2:15]2)=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 144749Ethyl 5-bromo-2-chlorobenzoateHCID 27580152-Cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

生成物 1

HCID 57422934Ethyl 2-chloro-5-cyclopropylbenzoate収率 92%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

In a schlenck tube, a mixture of ethyl 5-bromo-2-chlorobenzoate (7.60 mmol, 2 g), 2-cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (7.59 mmol, 1.3 g), Cs2CO3 (18.97 mmol, 6.18 g), PdCl2dppf.CH2Cl2 (0.76 mmol, 0.620 g) in dioxane (70 ml) and water (15 ml) was heated for 2 hours at 110° C., under argon atmosphere. The solvent was evaporated and the mixture was extracted between ethyl acetate and water. The crude mixture was purified by chromatography over SiO2 eluting hexane/ethyl acetate mixtures and affording 1.5 g (yield 92%) of the expected product.

後処理

  1. customThe solvent was evaporated
  2. extractionthe mixture was extracted between ethyl acetate and water
  3. customThe crude mixture was purified by chromatography over SiO2
  4. washeluting hexane/ethyl acetate mixtures

出典と根拠

ORDレコード
ord-3f7a1f5c32b142a0a07a8e28ccfefc8f
出典データセット
uspto-grants-2013_09
特許番号
US08536165B2

関連ノート

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