Dichloromethane → (2,4-Dichloro-phenyl)(3-methyl-6-m-tolyl-benzofuran-2-yl)methanone

HRID 1717651

Reaktionsgleichung

Reaktionsgleichung von HRID 1717651
Br[C:2]1[CH:21]=[CH:20][C:5]2[C:6]([CH3:19])=[C:7]([C:9]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=3[Cl:18])=[O:10])[O:8][C:4]=2[CH:3]=1.[CH3:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1.ClCCl.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C>[Cl:18][C:12]1[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=1[C:9]([C:7]1[O:8][C:4]2[CH:3]=[C:2]([C:27]3[CH:28]=[C:23]([CH3:22])[CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][C:5]=2[C:6]=1[CH3:19])=[O:10]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27339503-Tolylboronic acidHCID 59788907(6-Bromo-3-methyl-benzofuran-2-yl)(2,4-dichloro-phenyl)methanone

Produkt 1

HCID 11280888(2,4-Dichloro-phenyl)(3-methyl-6-m-tolyl-benzofuran-2-yl)methanoneAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A solution of (6-Bromo-3-methyl-benzofuran-2-yl)-(2,4-dichloro-phenyl)-methanone (50 mg, 0.13 mmol) in toluene (1.5 mL) and ethanol (1.5 mL) was degassed with argon for 15 min. At this time, 3-methyl benzene boronic acid (21.2 mg, 0.16 mmol, 1.2 eq) was added followed by [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium(II), complex with dichloromethane (1:1) (10.6 mg, 0.01 mmol, 0.1 eq) and 2M aqueous Na2CO3 (0.21 mL, 3 eq). The reaction was bubbled with argon for another 5 min and then heated to 85° C. for 4 h. The reaction was diluted with ethyl acetate, washed with water, brine, and dried over sodium sulfate. The solvent was removed at reduced pressure and purified on the pre-HPLC to afford 35.6 mg (69%) of a yellow solid as the product. 1H-NMR (CDCl3): δ 7.72 (d, J=8.0 Hz, 1H), 7.65 (s, 1H), 7.57 (dd, J=1.6, 8.0 Hz, 1H), 7.50 (d, J=1.9 Hz, 1H), 7.58 to 7.53 (m, 4H), 7.33 (t, 1H), 7.18 (d, J=7.2 Hz, 1H), 2.56 (s, 3H), 2.42 (s, 3H); LC-MS (MH+=395/397).

Aufarbeitung

  1. customThe reaction was bubbled with argon for another 5 min
  2. additionThe reaction was diluted with ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed at reduced pressure
  6. custompurified on the pre-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-3b55d410d8584280b4d5791c1fe74eeb
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803956B2

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