Acetic Acid → HCID 66700105, compound

Referring to Scheme 10, methylmagnesium iodide (14.12 mL, 3 M in Et2O, 42.4 mmol) was added to a stirred solution of 2,6-dibromo-9H-xanthen-9-one (7-2) (10 g, 28.2 mmol) in THF (30 mL) at 0° C. The reaction mixture was allowed to warm up to rt and stirred for 2 h. The reaction mixture was cooled to 0° C. and quenched with saturated NH4Cl solution (250 mL) and stirred for 30 min. The volatiles were removed in vacuo. The residue was taken up in CHCl3 (200 mL), and the organic layer was separated and the aqueous phase was extracted with CHCl3 (2×200 mL) and combined organics was dried over MgSO4, filtered and solvents removed in vacuo to crude product (9.46 g). The crude reaction was taken up in EtOAc (200 mL) and AcOH was added (20 mL) and the reaction mixture was stirred at room temperature for 3 h, the volatiles removed in vacuo and the residue was precipitated from isohexanes to give 2,6-dibromo-9-methylene-9H-xanthene (9-1) (6.43 g, 64.7% yield).

1. temperatureThe reaction mixture was cooled to 0° C.
2. customquenched with saturated NH4Cl solution (250 mL)
3. stirringstirred for 30 min
4. customThe volatiles were removed in vacuo
5. customthe organic layer was separated
6. extractionthe aqueous phase was extracted with CHCl3 (2×200 mL)
7. dry with materialcombined organics was dried over MgSO4
8. filtrationfiltered
9. customsolvents removed in vacuo to crude product (9.46 g)
10. customThe crude reaction
11. stirringthe reaction mixture was stirred at room temperature for 3 h
12. customthe volatiles removed in vacuo
13. customthe residue was precipitated from isohexanes

ORD record

ord-04b4563266da4f389117b04ef8811bed

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150554B2