Sodium Iodide → 2-Bromo-4-chloro-5-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethoxy]benzenamine

HRID 2088453Notes

Reaction equation

[NH2:1][C:2]1[C:3]([Br:10])=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].Br[CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN1C(=O)CCC1.O>[Br:10][C:3]1[CH:4]=[C:5]([Cl:9])[C:6]([O:8][CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[CH:7][C:2]=1[NH2:1]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 5-amino-4-bromo-2-chloro-phenol (0.338 g, 1.52 mmol) in NMP (5 ml) was added cesium carbonate (0.644 g, 1.97 mmol), sodium iodide (0.228 g, 1.52 mmol) and 2-bromoethoxy tertbutyldimethylsilane (0.424 g, 1.97 mmol). The mixture was heated to 100° C. for two hours, then cooled to room temperature. Water was added and the mixture was extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the residue by flash chromatography (hex:EtOAc/8:2) gave 2-bromo-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-4-chloro-phenylamine (0.505 g, 78%) as a white solid.

Workup

temperaturecooled to room temperature
extractionthe mixture was extracted with EtOAc
washThe combined organic extracts were washed with water and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated to dryness under reduced pressure
customPurification of the residue by flash chromatography (hex:EtOAc/8:2)

Sources & evidence

ORD record: ord-3da703f97f4e4af79efbc04b0e0d30d4
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08435990B2

Reaction notes

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