1,2-Dimethoxyethane → Biphenyl
Reaction equation
Br[C:2]1[C:7]([C:8]([CH3:11])([CH3:10])C)=[CH:6][CH:5]=[CH:4][C:3]=1S(N)(=O)=O.B(O)O.[C:19](=O)(O)[O-].[Na+].[Cl-].[NH4+].[CH2:26]([CH2:29]OC)OC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[C:8]1([C:7]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:10]=[CH:29][CH:26]=[CH:19][CH:11]=1Participants
Conditions
- Temperature
- 90 °C
Procedure
A degassed solution of 2-bromo tert-butylbenzenesulfonamide (IV) (15.6 g, 53.5 mmol) and tetrakis(triphenylphosphine)palladium (3.1 g, 2.7 mmol) in dimethoxyethane (270 mL) was stirred at room temperature for 5 minutes. Boronic acid V (purchased from Omega Chemical Company Inc.) (10 g, 53.5 mmol) and a 2M solution of sodium bicarbonate (53 mL) were then added and the mixture was heated to 90° C. and stirred at this temperature for 24 hours. The mixture was then cooled down and a saturated solution of ammonium chloride (300 mL) and ethyl acetate (300 mL) were added. The separated aqueous layer was extracted with ethyl acetate (3×100 mL) and the combined organic layers were dried (MgSO4 anh.), filtered and evaporated. Flash chromatography of the residue (EtOAc-hexanes 1:1) yielded biphenyl compound VI.
Workup
- temperatureThe mixture was then cooled down
- extractionThe separated aqueous layer was extracted with ethyl acetate (3×100 mL)
- dry with materialthe combined organic layers were dried (MgSO4 anh.)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-5d5351c6d0534159baab809fb6bbfcaf
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06277839B1
Reaction notes
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