1-(5-bromo-2-methoxyphenyl)ethanone → 1-(5-Bromo-2-methoxyphenyl)ethan-1-ol

An oven dried 500 mL flask, was charged under nitrogen with (S)-2-methyl-CBS-oxazaborolidine 1M in toluene (2.18 mL) and dissolved in CH2Cl2 (100 mL). Me2-BH3 (13.10 mL, 26.20 mmol) was then added and cooled reaction to −30° C. then stirred for 15 minutes. 5-Bromo-2-methoxyacetophenone (5 g, 21.83 mmol) was dissolved in CH2Cl2 (10 mL) and slowly added via addition funnel to the previous solution. The resulting reaction was stirred at −30° C. for 1 hour. The solution was carefully quenched with MeOH, the solvent was removed in vacuo and the residue was purified by flash column chromatography (20% EtOAc in hexanes) to provide the desired product (5 g, 100%) as a clear oil. 1H NMR (400 MHz, CDCl3): δ 1.47 (d, J=6.41 Hz, 3H), 2.44 (d, J=5 Hz, 1H), 3.84 (s, 3H), 5.03–5.11 (m, 1H), 6.74 (d, J=8.7 Hz, 1H), 7.33 (dd, J=8.7, 2.5 Hz, 1H), 7.48 (d, J=2.5 Hz, 1H).

1. customAn oven dried 500 mL flask
2. additionwas charged under nitrogen with (S)-2-methyl-CBS-oxazaborolidine 1M in toluene (2.18 mL)
3. dissolutiondissolved in CH2Cl2 (100 mL)
4. additionMe2-BH3 (13.10 mL, 26.20 mmol) was then added
5. temperaturecooled
6. customreaction to −30° C.
7. additionslowly added via addition funnel to the previous solution
8. customThe resulting reaction
9. stirringwas stirred at −30° C. for 1 hour
10. customThe solution was carefully quenched with MeOH
11. customthe solvent was removed in vacuo
12. customthe residue was purified by flash column chromatography (20% EtOAc in hexanes)

ORD record

ord-4f8e67819cb4485f841870c8c670d517

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07148226B2