Sulfuric acid, dibutyl ester → HCID 12502679, compound

To a stirred solution of 3,4-dibromothiophene (4.60 g, 20.90 mmol) in dry Et2O (50 mL) at -78° C. was dropwise added n-BuLi (2.5 M, 16.72 mL, 41.80 mmol) under Ar. After stirring for 15 min, a solution of freshly distilled di-n-butyl sulfate in dry Et2O (10 mL) was dropwise added through an addition funnel. The mixture was allowed to warm to room temperature and stirred overnight. 30 mL of 12 M NH4OH was added to the mixture. After stirring for 1 h, the mixture was partitioned between H2O and Et2O. The organic layer was separated and washed with H2O, brine and dried (MgSO4). Removal of the solvent under reduced pressure afforded the title compound as an oil (2.50 g, 60%).

1. customat -78° C.
2. stirringstirred overnight
3. stirringAfter stirring for 1 h
4. customthe mixture was partitioned between H2O and Et2O
5. customThe organic layer was separated
6. washwashed with H2O, brine
7. dry with materialdried (MgSO4)
8. customRemoval of the solvent under reduced pressure

ORD record

ord-dd6057357dcc4a0582932ceb54bf896d

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06017952