Dimethylformamide → HCID 21914339, compound

HRID 1245856Notes

Reaction equation

HRID 1245856 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-c0447e79f917412e94d668cbb5e4908b
Source dataset
uspto-grants-2006_10
Patent number
US07125896B2

Reaction notes

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