Tetrahydrofuran → Ethyl 3-chloro-4-(2-methylpropyl)benzoate

반응식

[Br-].[CH2:2]([Zn+])[CH:3]([CH3:5])[CH3:4].C1COCC1.Br[C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][C:14]=1[Cl:24]>>[Cl:24][C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][C:13]=1[CH2:2][CH:3]([CH3:5])[CH3:4])[C:17]([O:19][CH2:20][CH3:21])=[O:18]

참가 물질

반응물 3

HCID 8028Tetrahydrofuran

HCID 12594301Ethyl 4-bromo-3-chlorobenzoate

HCID 178448254HCID 178448254, 화합물

생성물 1

HCID 59316731Ethyl 3-chloro-4-(2-methylpropyl)benzoate

실험 절차

A solution of isobutylzinc bromide in THF (0.5 M, 30 mL, 15.0 mmol) was added under argon to ethyl 4-bromo-3-chlorobenzoate (D22) (2.00 g, 7.60 mmol) and then 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (930 mg, 1.14 mmol) was added. The reaction was heated to reflux for 4.5 h. The mixture concentrated in vacuo and the residue partitioned between ethyl acetate (125 mL) and water (125 mL). A solid formed, which was filtered off and discarded. The organic layer was washed with water (100 mL), dried (phase separator) and concentrated in vacuo. The crude product was purified by silica chromatography, eluting with 0-5% EtOAc in hexane over 30 minutes to give the title compound as a colourless oil (1.76 g, 7.33 mmol). δH (d6-DMSO, 400 MHz): 7.91 (1H, d), 7.80 (1H, dd), 7.46 (1H, d), 4.30 (2H, q), 2.66 (2H, d), 1.88-2.01 (1H, m), 1.32 (3H, t), 0.89 (6H, d). MS (ES): no mass ion observed.