Dimethylformamide → HCID 21914339, compound

HRID 2421378Notes

Reaction equation

HRID 2421378 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].CN(C)C=O>O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:16][CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 21914339HCID 21914339, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Bromophenol (1.88 g), anhydrous potassium carbonate (1.51 g), (2-bromoethoxy)-(tert-butyl)dimethylsilane (2.61 g) and dimethylformamide (30 ml) were heated for 20 h at 90° C., cooled, poured into water (100 ml), extracted with ethyl acetate, the organic phase washed with water, brine, dried (MgSO4) and evaporated to dryness. The residue was purified by column chromatography eluting with 1:9 ether/isohexane to give the product as a crystalline solid (1.68 g).

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washthe organic phase washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography
  7. washeluting with 1:9 ether/isohexane

Sources & evidence

ORD record
ord-71535d74ecba44a2afb4ed7da6661ae6
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

Loading…