Dichloromethane → HCID 69288939, compound

HRID 2184348Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10](I)=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[C:23]([O:28][CH3:29])(=[O:27])[C:24]([CH3:26])=[CH2:25].ClCCl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:29][O:28][C:23](=[O:27])[C:24]([CH3:26])=[CH:25][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]2[CH:14]=[CH:15][CH:16]=[C:2]([F:1])[CH:3]=2)=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 1.2 g (3.7 mmol) of 1-(3-fluorobenzyloxy)-4-iodo-benzene, 2.06 g (14.9 mmol) of potassium carbonate and 1.70 g (52.8 mmol) of tetrabutyl ammonium bromide in 10 ml of dimethylformamide is treated under Ar with 48 mg (0.21 mmol) of palladium-(II)-acetate. 1.49 g (14.9 mmol) of methyl methacrylate is added and the mixture heated at 90° C. for about 40 min. The reaction mixture is poured into 150 ml dichloromethane, filtered and washed successively with 0.1 molar hydrochloric acid, saturated aqueous sodium hydrogencarbonate and water. The solution is dried over magnesium sulfate. Flash chromatography (silica gel, hexane/ethyl acetate 95:5) yields 461 mg (42%) of a colorless solid. MS: m/e=301.3 (M++H).

Workup

filtrationfiltered
washwashed successively with 0.1 molar hydrochloric acid, saturated aqueous sodium hydrogencarbonate and water
dry with materialThe solution is dried over magnesium sulfate

Sources & evidence

ORD record: ord-92939a72af04404f9c66fb0d34fcee2b
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900354B2

Reaction notes

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