Dichloromethane → HCID 18182814, compound

HRID 1359231Notes

Reaction equation

HRID 1359231 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([Cl:12])=[C:7]([O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:6]=[CH:5]2.[O:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH:22]=[C:21]1B(O)O.ClCCl.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[O:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH:22]=[C:21]1[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([Cl:12])=[C:7]([O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:6]=[CH:5]2

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 2776266Benzo[b]furan-2-boronic acidHCID 18182792Ethyl 2-[(6-bromo-1-chloro-2-naphthyl)oxy]acetate

Product 1

HCID 18182814HCID 18182814, compoundYield 45.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Following the procedure described in Step 1 of Example 1, ethyl 2-[(6-bromo-1-chloro-2-naphthyl)oxy]acetate (3.79 g, 11.0 mmol) and 2-benzofuranboronic acid (2.14 g, 13.2 mmol) were coupled in the presence of [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium (II) complex with dichloromethane (1:1) (0.534 g, 0.654 mmol) and potassium carbonate (3.07 g, 22.2 mmol) in dioxane (110 mL) and water (11 mL). Purification by flash chromatography using 2-5% ethyl acetate in hexane as an eluant furnished ethyl 2-{[6-(1-benzofuran-2-yl)-1-chloro-2-naphthyl]oxy}acetate as a cream-colored solid (1.91 g), mp 140-142° C. 1HNMR (300 MHz, DMSO-d6): δ8.5 (s, 1H), 8.2 (s, 2H), 8.1 (d, 1H, J=8.3 Hz), 7.75-7.85 (m, 2H), 7.7 (s, 1H), 7.5 (d, 1H, J=8.3 Hz), 7.25-7.4 (m. 2H), 5.1 (s, 2H), 4.2 (q, 2H, J=7.5 Hz), and 1.25 ppm (t, 2H, J=7.5 Hz).

Workup

  1. customPurification by flash chromatography

Sources & evidence

ORD record
ord-3e58b64c4a104852a780f0cefb6b3d67
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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