Dimethyl Sulfoxide → HCID 53672092, compound

HRID 327963Notes

Reaction equation

HRID 327963 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+].CS(C)=O>CCOCC>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][O:10][C:7]1[CH:8]=[CH:9][C:2]([Br:1])=[C:3]([CH:4]=[O:5])[CH:6]=1)[CH3:19]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 3871792-Bromo-5-hydroxybenzaldehyde

Product 1

HCID 53672092HCID 53672092, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3.5 g (17.4 mmol) of 2-bromo-5-hydroxybenzaldehyde, 3.7 g (19 mmol) of ethyl 4-bromobutyrate, 5.5 g (40 mmol) of anhydrous, granular potassium carbonate, and 40 mL of dry dimethyl sulfoxide was stirred at room temperature for 5 hr and then kept at room temperature overnight. The resulting slurry was poured into ice-water and worked-up with ether in the usual manner giving an oil product which was flash-chromatographed on silica gel. Elution with 2:1 hexane-ether afforded 4.4 g (80.3%) of 4-(4-bromo-3-formylphenoxy)butanoic acid ethyl ester as an oil.

Workup

  1. waitkept at room temperature overnight
  2. customgiving an oil product which
  3. customwas flash-chromatographed on silica gel
  4. washElution with 2:1 hexane-ether

Sources & evidence

ORD record
ord-85ac052da31b4e53b73a0e39535e6c4e
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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