Allyl bromide → HCID 58653725, compound

HRID 2220235Notes

Reaction equation

HRID 2220235 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[CH:8]=[CH2:9].[CH2:11]([O:13][C:14](=[O:33])[C:15]([OH:32])([C:28]([F:31])([F:30])[F:29])[CH2:16][C:17]([C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[OH:27])([CH3:19])[CH3:18])[CH3:12]>CN(C=O)C>[CH2:11]([O:13][C:14](=[O:33])[C:15]([OH:32])([C:28]([F:29])([F:30])[F:31])[CH2:16][C:17]([C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[O:27][CH2:9][CH:8]=[CH2:7])([CH3:19])[CH3:18])[CH3:12]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 58653728HCID 58653728, compound

Product 1

HCID 58653725HCID 58653725, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (4.15 g, 30 mmol) and allyl bromide (2.16 ml, 25 mmol) are added to a solution of 4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethyl-valeric acid ethyl ester (5.36 g, 15.84 mmol) in DMF (50 ml) while being cooled with ice. After 2 hours at 2° C. and after 2 hours at room temperature, the batch is poured into ice water and extracted with hexane-ether 2:1. The combined organic extracts are dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with hexane-ethyl acetate yields 5.7 g of the product.

Workup

  1. temperaturewhile being cooled with ice
  2. waitafter 2 hours at room temperature
  3. extractionextracted with hexane-ether 2:1
  4. dry with materialThe combined organic extracts are dried (Na2SO4)
  5. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-d3eae824e04046a5a47f58a9c25ba30e
Source dataset
uspto-grants-2008_08
Patent number
US07417056B2

Reaction notes

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