Sodium Iodide → HCID 59377706, compound

HRID 1691791Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[C:10]([OH:12])[C:9]([F:13])=[CH:8][C:7]=1[Br:14])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].Br[CH2:25][CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>CN1C(=O)CCC1.O>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH2:25][CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[C:9]([F:13])=[CH:8][C:7]=1[Br:14])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (2-bromo-4-fluoro-5-hydroxy-phenyl)-acetic acid ethyl ester (0.42 1 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 tert-butyldimethylsilane (0.424 g, 1.97 mmol). The mixture was heated at 100° C. for two hours. After cooling to room temperature, water was added and the product 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 residue by flash chromatography (hexanes:EtOAc/8:2) gave {2-bromo-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-4-fluoro-phenyl}-acetic acid ethyl ester (0.508 g, 77%) as a white solid.

Workup

temperatureAfter cooling to room temperature
extractionthe product 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 residue by flash chromatography (hexanes:EtOAc/8:2)

Sources & evidence

ORD record: ord-ae50fcc3d39e402eaaf239c5bb3b1669
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153808B2

Reaction notes

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