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

HRID 29234

Reaction equation

HRID 29234 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

HCID 11280888(2,4-Dichloro-phenyl)(3-methyl-6-m-tolyl-benzofuran-2-yl)methanoneYield 69.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-9ecc41b22e8544a89f7698225a4656f8
Source dataset
uspto-grants-2008_09
Patent number
US07420066B2

Linked notes

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