Sodium Iodide → Tert-butyl-[2-(2,3-difluoro-4-methyl-5-nitro-phenoxy)-ethoxy]-dimethyl-silane

HRID 2065746Notes

Reaction equation

[F:1][C:2]1[C:7]([F:8])=[C:6]([CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[OH:13].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].Br[CH2:23][CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>CN1C(=O)CCC1.O>[C:29]([Si:26]([O:25][CH2:24][CH2:23][O:13][C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[C:6]([CH3:9])=[C:7]([F:8])[C:2]=1[F:1])([CH3:28])[CH3:27])([CH3:32])([CH3:31])[CH3:30]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2,3-difluoro-4-methyl-5-nitro-phenol (1.02 g, 5.39 mmol) in NMP (10 ml) was added cesium carbonate (2.28 g, 7.01 mmol), sodium iodide (0.807 g, 5.39 mmol) and 2-bromoethoxy tertbutyldimethylsilane (1.5 ml, 7.01 mmol). The mixture was heated at 100° C. for one hour, then cooled to room temperature. Water was added and the mixture was extracted with EtOAc. The combined extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the crude product by flash chromatography (hexanes:EtOAc 9:1) gave 1.16 g (62%) of tert-butyl-[2-(2,3-difluoro-4-methyl-5-nitro-phenoxy)-ethoxy]-dimethyl-silane as a tan solid.

Workup

temperaturecooled to room temperature
extractionthe mixture was extracted with EtOAc
washThe combined extracts were washed with water and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated to dryness under reduced pressure
customPurification of the crude product by flash chromatography (hexanes:EtOAc 9:1)

Sources & evidence

ORD record: ord-14eb0a2d2b3646d48bf375058c96034b
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288552B2

Reaction notes

Loading…