Dimethylformamide → 5-Ethyl-2-fluorobenzaldehyde

Temperature

-60 °C

To a solution of 1-ethyl-4-fluorobenzene (10 g, 80.6 mmol) and PMDTA (17 mL) in THF (60 mL) cooled to −78° C. was added 1.6 M n-butyl lithium (56 mL, 89 mmol) dropwise and the mixture stirred for 40 min at −60° C. Mixture cooled to −78° C. and added DMF (16 mL, 202 mmol) before allowing the mixture to warm to 23° C. Quenched with aqueous NH4Cl and extracted with EtOAc (3×50 mL). Organic layer was washed with H2O and brine before concentrating to afford 11.6 g of Intermediate 311.2. 1H-NMR (CDCl3)=1.18 (t, 3 H), δ 2.58 (q, 2 H), δ 7.04 (t, 1 H), δ 7.35 (m, 1 H), δ 7.62 (m, 1 H), δ 10.31 (s, 1 H).

1. temperatureMixture cooled to −78° C.
2. temperatureto warm to 23° C
3. customQuenched with aqueous NH4Cl
4. extractionextracted with EtOAc (3×50 mL)
5. washOrganic layer was washed with H2O and brine
6. concentrationbefore concentrating

ORD record

ord-0d78b5a1926e44da800df9816cdb650b

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576098B2