4-Bromo-2-chloro-1-(2-chloroethoxy)benzene → 4-bromo-2-chloro-1-(ethenyloxy)Benzene

To a solution of 4-bromo-2-chloro-1-(2-chloro-ethoxy)-benzene (5.84 g, 17.4 mmol, 1 eq.) in DMF (22 mL), sodium hydride 60% dispersion in mineral oil (1.40 g, 34.9 mmol, 2 eq.) was added portionwise at r.t. The resulting mixture was stirred at r.t. for 18 hours. The mixture was partitioned between water (70 mL) and AcOEt (250 mL). The layers were separated and the org. layer was washed with water (4×100 mL), dried over MgSO4, filtered, and concentrated in vacuo. To a solution of the residue in DMF (22 mL), sodium hydride 60% dispersion in mineral oil (1.40 g, 34.9 mmol, 2 eq.) was added portionwise at r.t. The resulting mixture was stirred at r.t. for 48 hours. The mixture was partitioned between water (70 mL) and AcOEt (250 mL). The layers were separated and the org. layer was washed with water (4×100 mL), dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flashmaster (column: 100 g, flow: 45 mL/min, 30 fractions of 45 mL, Heptane 100% to Heptane+5% AcOEt) to give 4-bromo-2-chloro-1-vinyloxy-benzene as a colorless oil.

1. customThe mixture was partitioned between water (70 mL) and AcOEt (250 mL)
2. customThe layers were separated
3. washlayer was washed with water (4×100 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. stirringThe resulting mixture was stirred at r.t. for 48 hours
8. customThe mixture was partitioned between water (70 mL) and AcOEt (250 mL)
9. customThe layers were separated
10. washlayer was washed with water (4×100 mL)
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. concentrationconcentrated in vacuo
14. customThe residue was purified by flashmaster (column: 100 g, flow: 45 mL/min, 30 fractions of 45 mL, Heptane 100% to Heptane+5% AcOEt)

ORD record

ord-e831fa3aed664eada6dc0d106e500794

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09255090B2