Formaldehyde → 2,2-Bis(3-bromophenyl)propane-1,3-diol

Temperature

95 °C

A mixture of the crude 2,2-bis(3-bromophenyl)oxirane (7.4 g, 20.90 mmol) and p-toluenesulfonic acid monohydrate (360 mg, 2.1 mmol) in toluene (25 mL) was stirred at 95° C. for 1 h. The solution was washed with aq NaHCO3 (10 mL) and water (20 mL). The organic layer was dried and concentrated. The residue was dissolved in EtOH (20 mL). To the solution was added formaldehyde (15.56 mL, 209 mmol, 37% aqueous solution) and K2CO3 (1.44 g, 10.45 mmol). The mixture was stirred at 85° C. for 12 h. After cooling to room temperature, the reaction mixture was diluted with water (50 mL) and extracted with dichloromethane (60 mL×4). The combined organic layers were dried and concentrated. The residue was purified by column chromatography (on silica gel, eluent with Petroleum ether˜Petroleum ether: EtOAc=2:1) to afford 4.6 g of 2,2-bis(3-bromophenyl)propane-1,3-diol (11.9 mmol, 57% after two steps). LC/MS: [M−18+1]=368. 1HNMR (CDCl3), 400 MHz: δ 2.53 (brs, 2H), 2.41 (s, 4H), 7.09-7.20 (m, 4H), 7.36-7.40 (m, 4H).

1. washThe solution was washed with aq NaHCO3 (10 mL) and water (20 mL)
2. customThe organic layer was dried
3. concentrationconcentrated
4. dissolutionThe residue was dissolved in EtOH (20 mL)
5. stirringThe mixture was stirred at 85° C. for 12 h
6. temperatureAfter cooling to room temperature
7. extractionextracted with dichloromethane (60 mL×4)
8. customThe combined organic layers were dried
9. concentrationconcentrated
10. customThe residue was purified by column chromatography (on silica gel, eluent with Petroleum ether˜Petroleum ether: EtOAc=2:1)

ORD record

ord-d293b7b710e342418f363c60887833f9

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08937150B2