Sulfuric Acid → (4-Methoxyphenyl)boronic acid
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Mg].C([O:13][B:14](OCC)[O:15]CC)C.S(=O)(=O)(O)O>C(OCC)C.O>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([B:14]([OH:15])[OH:13])=[CH:3][CH:4]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -70 °C
Procedure
100 ml of a solution of 10 g of p-bromoanisole in anhydrous diethyl ether is added dropwise under reflux to a suspension, under inert gas, of 1.3 g of magnesium turnings in 5 ml of anhydrous diethyl ether, and the mixture is left under reflux for 2 hours. The reaction medium is then poured into a solution of 9.02 ml of triethylborate in 60 ml of anhydrous ether cooled down to -70° C. After agitation for 1 hour at -70° C., then for 1 hour at ambient temperature, the solution is poured into a mixture containing 11 ml of sulphuric acid and 50 g of ice and water and agitation is carried out for 1 hour. The organic phase is extracted with 100 ml of a saturated aqueous solution of sodium bicarbonate, the aqueous phases are combined, reacidified with 6N hydrochloric acid, extracted with ether, dried and evaporated under reduced pressure. 3.9 g of expected product is obtained.
Workup
- waitthe mixture is left
- temperatureunder reflux for 2 hours
- waitfor 1 hour at ambient temperature
- additionthe solution is poured into a mixture
- waitis carried out for 1 hour
- extractionThe organic phase is extracted with 100 ml of a saturated aqueous solution of sodium bicarbonate
- extractionextracted with ether
- customdried
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-a3b336f7091f4328bf72a2d0151ab22b
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06147119
Reaction notes
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