Imidazole → (2-Allyl-3-bromo-6-chloro-5-(4-methoxybenzyl)phenoxy)(tert-butyl)dimethylsilane

HRID 2206774Notes

Reaction equation

[CH2:1]([C:4]1[C:9]([Br:10])=[CH:8][C:7]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:6]([Cl:20])[C:5]=1[OH:21])[CH:2]=[CH2:3].[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].N1C=CN=C1>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH2:1]([C:4]1[C:9]([Br:10])=[CH:8][C:7]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:6]([Cl:20])[C:5]=1[O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of phenol 185 (2.29 g, 6.23 mmol) in DMF (30 mL) were added tert-butyldimethylsilyl chloride (1M in THF, 9.35 mL, 9.35 mmol), imidazole (1.3 g, 18.7 mmol) and catalytic DMAP. The mixture was stirred at 50° C. for 15 hours. The mixture was extracted with EtOAc/aq. 50% NaCl solution (100 mL/500 mL). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the product 186 (2.57 g, 86%).

Workup

extractionThe mixture was extracted with EtOAc/aq
washThe organic layer was washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-1edccaa93537468abcb64d3e613c7bec
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371303B2

Reaction notes

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