Iodine → HCID 178436979, compound

HRID 2361552Notes

Reaction equation

[Mg].II.Br[CH2:5][CH2:6]Br.Br[C:9]1[CH:17]=[C:16]([CH2:18][CH3:19])[C:12]([N:13]([CH3:15])[CH3:14])=[C:11]([CH2:20][CH3:21])[CH:10]=1.[P:22]([O-:29])(OCC)OCC>O1CCCC1.C(OCC)(=O)C.O>[CH3:14][N:13]([CH3:15])[C:12]1[C:11]([CH2:20][CH3:21])=[CH:10][C:9]([PH:22](=[O:29])[C:9]2[CH:17]=[C:16]([CH2:18][CH3:19])[C:12]([N:13]([CH3:15])[CH3:14])=[C:11]([CH2:20][CH3:21])[CH:10]=2)=[CH:17][C:16]=1[CH2:5][CH3:6]

Participants

Conditions

Temperature: 40 °C

Procedure

Under an argon atmosphere, a solution of magnesium (2.8 g, 1.0 equivalent), a small amount of iodine and a small amount of 1,2-dibromoethane in tetrahydrofuran (15 mL) was stirred at room temperature for 30 min. A solution of 4-bromo-2,6-diethyl-N, N-dimethylaniline (29.4 g, 0.115 moL) synthesized in Reference Example 3 in tetrahydrofuran (50 mL) was added to the mixture at 20° C. to 25° C. over 1 hr, and the mixture was stirred at 40° C. for 1 hr. Then, a solution of diethyl phosphite (4.01 g, 0.25 equivalent) in tetrahydrofuran (8 mL) was added at 20° C. to 25° C. over 1 hr. Water (90 mL) was added to the mixture at 5° C. to 10° C., and then ethyl acetate (100 mL) was added to the mixture. The mixture was partitioned, and the organic layer was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 100 g, n-hexane/ethyl acetate) to give the title compound (8.34 g, colorless liquid). yield 72%.

Workup

additionwas added to the mixture at 20° C. to 25° C. over 1 hr
customThe mixture was partitioned
concentrationthe organic layer was concentrated under reduced pressure
customThe residue was purified by column chromatography (silica gel 100 g, n-hexane/ethyl acetate)

Sources & evidence

ORD record: ord-aa71a2639bc048bf9b9ad11746da0f01
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691718B2

Reaction notes

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