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Sodium Iodide → HCID 59377706, compound

HRID 1691791
Notes
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Reaction equation

HRID 1691791 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 59377674HCID 59377674, compound

Product 1

HCID 59377706HCID 59377706, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 13387N-methyl-2-pyrrolidoneSolvent

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

  1. temperatureAfter cooling to room temperature
  2. extractionthe product was extracted with EtOAc
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes