Potassium Carbonate → Methyl 2,2'-dimethyl-1,1'-biphenyl-4-carboxylate
Reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].[C:13]1([CH3:22])[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[CH3:12][C:3]1[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:2]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH3:22]Participants
Conditions
- Temperature
- 100 °C
Procedure
A mixture of methyl 4-bromo-3-methylbenzoate (25.0 g, 110 mmol), o-tolylboronic acid (16.5 g, 120 mmol) and potassium carbonate (50 g, 360 mmol) in dioxane/water (300 mL:200 mL) was purged with nitrogen for 1 hour. [1,-bis(Diphenylphosphino) ferrocene]dichloropalladium [II] (4.5 g, 5.5 mmol) was added. The reaction mixture was heated to 100° C. with vigorous stirring for 3.5 hours, then cooled and filtered through Celite® (Celite Corp., Santa Barbara, Calif.). The cake was washed with ethyl acetate (500 mL). The combined organic phases were washed with 1N sodium hydroxide (500 mL) and brine (500 mL), dried over anhydrous potassium carbonate, and concentrated in vacuo to afford a dark oil (28.6 g). Purification by flash chromatography using 2% ethyl acetate in hexanes as solvent provided the title compound (24.7 g, 93%) as a pale yellow oil. MS [(+)ESI, m/z]: 241 [M+H]+ HRMS [(+)ESI, m/z]: 241.12205 [M+H]+. Calcd for C16H17O2: 241.12286 Anal. Calcd for C16H16O2: C, 79.97; H, 6.71. Found: C, 79.67; H, 6.61.
Workup
- customwas purged with nitrogen for 1 hour
- temperaturecooled
- filtrationfiltered through Celite® (Celite Corp., Santa Barbara, Calif.)
- washThe cake was washed with ethyl acetate (500 mL)
- washThe combined organic phases were washed with 1N sodium hydroxide (500 mL) and brine (500 mL)
- dry with materialdried over anhydrous potassium carbonate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-461e28f1b5b3424bb615234ba8548c48
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691848B2
Reaction notes
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