4-Chlorobenzaldehyde → HCID 67212218, compound

Temperature

-78 °C

Diisopropylamine (11.7 mL, 83.3 mmol) was dissolved in THF (200 mL) under a nitrogen atmosphere at 0° C. and n-butyllithium (52.5 mL, 1.6 M in hexanes, 84.0 mmol) was added. The solution was stirred for 1 h, cooled to −78° C. and 4-chloropyridine hydrochloride (5.00 g, 33.3 mmol) was added portionwise. The reaction mixture was stirred 2 h and 4-chlorobenzaldehyde (4.68 g, 33.3 mmol) was added. The reaction mixture was allowed to warm slowly to room temperature and stirred for 3 d. Sat aq NH4Cl solution (20 mL) was iii added and the reaction mixture was poured into 1 M aq Na2CO3 solution (500 mL). The layers were separated and the aq layer was extracted with DCM (2×500 mL). The combined organic layers were dried (MgSO4) and the solvents were removed in vacuo to give (4-chlorophenyl)-(4-chloro-pyridin-3-yl)-methanol (7.57 g, 89.4%) as a light brown solid.

1. stirringThe reaction mixture was stirred 2 h
2. temperatureto warm slowly to room temperature
3. stirringstirred for 3 d
4. additionadded
5. customThe layers were separated
6. extractionthe aq layer was extracted with DCM (2×500 mL)
7. dry with materialThe combined organic layers were dried (MgSO4)
8. customthe solvents were removed in vacuo

ORD record

ord-9c71d661e6894b9aa5a0248544e66e56

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08633318B2