3,4-Dibromothiophene → HCID 10536833, Verbindung

A solution of 3,4-dibromothiophene (6.0 g, 24.8 mmol) in 10 mL of ether was cooled to -78° C. and trated with n-butyllithium (9.92 mL, 2.5M solution in hexanes, 24.8 mmol). While holding the temperature at -78° C., the reaction was stirred for 15 minutes, then 2.9 g (24.8 mmol) of N-methyl-N-methoxypropionamide was added and the reaction was stirred for 1 hour. The reaction was quenched with satd NH4Cl, and the mixture was diluted with ether. The ether layer was separated, washed with water and brine, dried over MgSO4 and concentrated. The residue was triturated with hexanes, and the mixture was filtered. The solvent was removed to give 2.08 g of a tan solid. MS 236, 238 (M+NH4)+. NMR (CDCl3) δ:7.99 (d, J=3 Hz, 1H), 7.32 (d, J=3 Hz, 1H), 2.98 (q, J=7 Hz, 2H), 1.21 (t, J=7 Hz, 3H).

1. customat -78° C.
2. stirringthe reaction was stirred for 1 hour
3. customThe reaction was quenched with satd NH4Cl
4. additionthe mixture was diluted with ether
5. customThe ether layer was separated
6. washwashed with water and brine
7. dry with materialdried over MgSO4
8. concentrationconcentrated
9. customThe residue was triturated with hexanes
10. filtrationthe mixture was filtered
11. customThe solvent was removed

ORD-Eintrag

ord-a348106b0b6d43e3a45bb6ec8506f1c4

Quelldatensatz

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05597832