Tetrahydrofuran → 1-(4-Bromophenyl)but-2-yn-1-one

To an ice cold solution of 4-bromobenzaldehyde (1.3 g, 7 mmol) 0.5 M solution of propynyl magnesium bromide in THF (15 ml, 7.5 mmol) was added under N2. The mixture was stirred for 10 min, quenched with saturated NH4Cl solution and diluted to 50 ml with EtOAc. The organic layer was washed with H2O, dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was dissolved in 1,4-dioxane (25 ml). To it MnO2 (2 g) was added and the resulting suspension was stirred for 4 h at reflux. The mixture was filtered through Celite pad and the filtrate was evaporated to dryness and dried in vacuo to give the title compound (1.29 g, 83%) as a pale solid. 1H-NMR (CDCl3) 7.97 (d, 2H, J=9 Hz); 7.61 (d, 2H, J=9 Hz); 2.14 (s, 3H).

1. customquenched with saturated NH4Cl solution
2. additiondiluted to 50 ml with EtOAc
3. washThe organic layer was washed with H2O
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customThe filtrate was evaporated to dryness
7. dissolutionthe residue was dissolved in 1,4-dioxane (25 ml)
8. additionTo it MnO2 (2 g) was added
9. stirringthe resulting suspension was stirred for 4 h
10. temperatureat reflux
11. filtrationThe mixture was filtered through Celite pad
12. customthe filtrate was evaporated to dryness
13. customdried in vacuo

ORD record

ord-2690e8b98036482588599f7a8bafb0ee

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193716B2