Myristyl bromide → HCID 53836653, compound

HRID 247970Notes

Reaction equation

HRID 247970 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([F:12])[CH:6]=1.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15])=[C:7]([F:12])[CH:6]=1

Participants

5

Reactant 3

HCID 8208Myristyl bromideHCID 11430Potassium CarbonateHCID 10797559Methyl 2-(3-fluoro-4-hydroxyphenyl)acetate

Product 1

HCID 53836653HCID 53836653, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 23.0 g of product from Example 60, 34.6 g of 1-bromotetradecane, 54.6 g of potassium carbonate and 250 ml of acetone is heated at reflux temperature for 48 hours. The cooled reaction is filtered and concentrated in vacuo. The residue is purified by column chromatography (silica gel:0-4.5% ethyl acetate/hexane) to give 46.3 g of the desired product as colorless prisms.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 48 hours
  3. customThe cooled reaction
  4. filtrationis filtered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by column chromatography (silica gel:0-4.5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e851d14c4b2f472b8dd663dffaa6d5e5
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

Loading…