Styrene → P-Methoxystilbene

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH2:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:3][CH:4]=1

Participants

Reactant 3

HCID 7501Styrene

HCID 8471Triethylamine

HCID 696764-Iodoanisole

Product 1

HCID 1245920P-Methoxystilbene

Procedure

4-Iodoanisole (58 mg, 0.25 mmol) and styrene (43 μL, 0.375 mmol) were coupled using the procedure described above, but using triethylamine (0.375 mmol, 52 μL) in place of ethyldiisopropylamine, to give 100% conversion to (E)-4-methoxystilbene by GC analysis.

Sources & evidence

ORD record: ord-7ae5b94b9af240a9831caff3bee98b17
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233366B2

Reaction notes

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