Diiodomethane → HCID 57582366, compound

Diethyl zinc (1M in toluene, 23 ml, 23 mmol) was added under nitrogen with stirring to a solution of 2-bromo-4-fluoro-1-vinyloxy-benzene (Preparation 88, 1.0 g, 4.61 mmol) in dichloroethane (45 ml) at −10° C. (ice-salt-MeOH), taking care to maintain the temperature below 0° C. Diiodomethane (6.17 g, 23 mmol) in dichloroethane (10 ml) was then added via a syringe to the reaction mixture over 5 minutes ensuring that the reaction mixture remained at a temperature below +5° C. (internal temp). The reaction mixture was stirred at this temperature for twenty minutes and then allowed to attain room temperature and stirring was continued for 72 hours. The reaction was quenched with cold saturated ammonium chloride (aqueous solution) (5 ml) then the lower organic phase was removed, whilst the aqueous was extracted with a further dichloromethane (20 ml). The combined organic layers were dried over anhydrous Na2SO4 (s), filtered and evaporated in vacuo. Purification by column chromatography on silica gel eluting with tert-butyldimethyl ether:heptane 1:99 to 1:19 afforded almost pure title compound (93 mg, 9%).

1. temperatureto maintain the temperature below 0° C
2. customremained at a temperature below +5° C. (internal temp)
3. customto attain room temperature
4. stirringstirring
5. customThe reaction was quenched with cold saturated ammonium chloride (aqueous solution) (5 ml)
6. customthe lower organic phase was removed
7. extractionwhilst the aqueous was extracted with a further dichloromethane (20 ml)
8. dry with materialThe combined organic layers were dried over anhydrous Na2SO4 (s)
9. filtrationfiltered
10. customevaporated in vacuo
11. customPurification by column chromatography on silica gel eluting with tert-butyldimethyl ether:heptane 1:99 to 1:19

ORD record

ord-8a1eb565cc0346f98cafc7d7ccc5b971

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08134007B2