Acetic Acid → HCID 782859, compound

Morpholine (0.96 mL) and acetic acid (0.57 mL) are added to a solution of 3-bromo-4-fluorobenzaldehyde (2.03 g) in dichloroethane (40 mL). Sodium triacetoxyborohydride (3.18 g) is added in portions over an hour, and the reaction is stirred at room temperature for 18 hours. The reaction is quenched with a 1 N solution of NaOH (10 mL) and diluted with CH2Cl2 (100 mL). The organic layer is washed with 1 N NaOH (3×35 mL). The aqueous layers are back-extracted with CH2Cl2 (20 mL). The combined organic layers are extracted with 0.1 N HCl (6×25 mL). The combined aqueous layers are basified (pH=12) with 2 N NaOH, and the product is extracted with CH2Cl2 (6×25 mL). The combined organic layers are washed with brine (20 mL) and dried (MgSO4). The solution is concentrated in vacuo to afford 2.23 g (82%) of the title compound as a clear, colorless oil.

1. customThe reaction is quenched with a 1 N solution of NaOH (10 mL)
2. additiondiluted with CH2Cl2 (100 mL)
3. washThe organic layer is washed with 1 N NaOH (3×35 mL)
4. extractionThe aqueous layers are back-extracted with CH2Cl2 (20 mL)
5. extractionThe combined organic layers are extracted with 0.1 N HCl (6×25 mL)
6. extractionthe product is extracted with CH2Cl2 (6×25 mL)
7. washThe combined organic layers are washed with brine (20 mL)
8. dry with materialdried (MgSO4)
9. concentrationThe solution is concentrated in vacuo

ORD record

ord-0065271383da4e809144bc77316e1d0d

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06248739B1