Boron tribromide → HCID 86710791, compound
Reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([B:9]([OH:11])[OH:10])=[C:4]([O:12]C)[CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([B:9]([OH:10])[OH:11])=[C:4]([OH:12])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of (4-chloro-2-methoxy-5-methylphenyl)boronic acid (100 mg, 0.499 mmol) in DCM (2 mL) was cooled to 0° C. and BBr3 (0.142 mL, 1.497 mmol) was added. The mixture was then stirred at rt for 2 h. It was then poured into ice and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to obtain 150 mg (97% yield, 60% pure) of the desired product as a brown solid. 1H NMR (400 MHz, CDCl3) δ 7.59 (br. s., 1H), 7.11 (br. s., 1H), 4.30-4.11 (m, 1H), 4.01 (br. s., 1H), 2.37 (s, 3H).
Workup
- additionIt was then poured into ice
- extractionextracted with EtOAc
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-0463b5e58ce64803a4a94ba339edef3e
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906929B2
Reaction notes
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