Hydrochloric Acid → 1-Tert-butyl-3-iodo-2-methoxy-5-(1-phenylvinyl)benzene

HRID 530667Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[C:9](I)[CH:8]=[C:7]([I:12])[C:6]=1[O:13][CH3:14])([CH3:4])([CH3:3])[CH3:2].[C:15]1([C:21](B(O)O)=[CH2:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)(O)[O-].[Na+].Cl>C(COC)OC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([C:5]1[CH:10]=[C:9]([C:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH2:22])[CH:8]=[C:7]([I:12])[C:6]=1[O:13][CH3:14])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 1-tert-butyl-3,5-diiodo-2-methoxybenzene (4.94 g, 11.87 mmol) in dimethoxyethane (50 mL) and water (30 mL) was treated with 1-phenylvinylboronic acid (2.283 g, 15.43 mmol), tetrakis(triphenylphosphine)palladium(0) (0.686 g, 0.593 mmol) and sodium bicarbonate (2.492 g, 29.7 mmol) followed by heating at 100° C. for 3 hours. 1 N HCl was added and the mixture was extracted with ethyl acetate, then dried (Na2SO4), filtered and concentrated in vacuo to give crude product which was purified by silica gel flash chromatography eluting with 50:1 hexanes/ethyl acetate to give the title compound.

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customto give crude product which
customwas purified by silica gel flash chromatography
washeluting with 50:1 hexanes/ethyl acetate

Sources & evidence

ORD record: ord-47e6908f42bc48c199cb8c9e01e3afb7
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353091B2

Reaction notes

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