Dichloromethane → Ethyl 2-chloro-5-cyclopropylbenzoate

HRID 41999Notes

Reaction equation

HRID 41999 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

HCID 57422934Ethyl 2-chloro-5-cyclopropylbenzoateYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3f7a1f5c32b142a0a07a8e28ccfefc8f
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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