Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[O:9][CH3:10].[C:11]([OH:15])(=[O:14])[CH:12]=[CH2:13].C(N(CC)CC)C.Cl>CC#N.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:13]=[CH:12]/[C:11]([OH:15])=[O:14])=[CH:4][C:3]=1[O:9][CH3:10]Participants
7
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 1-bromo-4-iodo-2-methoxybenzene (L. A. Hasvold et al, US 2004/0254159, EXAMPLE 57B) (33.45 g, 107 mmol) in MeCN (100 mL) was added acrylic acid (9.61 g, 133 mmol), triethylamine (37.2 mL, 267 mmol) and palladium acetate (719 mg, 3.2 mmol). The reaction mixture was heated to 90° C. for 40 min, cooled to RT and poured into 2.4 L 1M HCl. After stirring for 30 min, the solid was filtered, heated to reflux in EtOH (230 mL), allowed to cool to RT and stirred overnight. The solid was filtered and washed with 1:1 EtOH hexane (50 mL) to give desired product. LRMS ESI+ (M+H)+ 257.0.
Workup
- temperaturecooled to RT
- filtrationthe solid was filtered
- temperatureheated
- temperatureto reflux in EtOH (230 mL)
- temperatureto cool to RT
- stirringstirred overnight
- filtrationThe solid was filtered
- washwashed with 1:1 EtOH hexane (50 mL)
Sources & evidence
- ORD record
- ord-ad4bef70c36e42c8963df88b4f8f42fd
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278322B2
Linked notes
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