Dimethylformamide → Methyl 3-ethenyl-1-naphthalenecarboxylate
Reaction equation
Br[C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH:16](B1OC(C)(C)C(C)(C)O1)=[CH2:17].CN(C=O)C.C([O-])([O-])=O.[Na+].[Na+]>C(O)CC>[CH:16]([C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)=[CH2:17]Participants
Conditions
- Temperature
- 90 °C
Procedure
Methyl 3-bromo-1-naphthalenecarboxylate (1 eq.) and 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1 eq.) were combined in a 2:1 (v/v) mixture of DMF:n-PrOH (0.1 M). To this solution was first added Pd(PPh3)2Br2 (0.05 eq.) followed by 2 N aq. Na2CO3 (2 eq.). The biphasic suspension was evacuated and back-filled three times with nitrogen before it was heated at 90° C. for 8 h. The now black suspension was cooled to RT, diluted with water and extracted with 1:1 (v/v) hexanes:ether. The combined organic extracts were then washed further with 1 N aq. NaOH, 10% aq. HCl, water and brine. This was then dried over Na2SO4 and filtered through a pad of silica gel. Concentration of the filtrate in vacuo afforded the crude title compound as a golden yellow oil.
Workup
- customThe biphasic suspension was evacuated
- additionback-filled three times with nitrogen before it
- temperatureThe now black suspension was cooled to RT
- additiondiluted with water
- extractionextracted with 1:1 (v/v) hexanes
- washThe combined organic extracts were then washed further with 1 N aq. NaOH, 10% aq. HCl, water and brine
- dry with materialThis was then dried over Na2SO4
- filtrationfiltered through a pad of silica gel
Sources & evidence
- ORD record
- ord-30039ae241a349f78552fa9606c00a66
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889714B2
Reaction notes
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