Hydrogen Bromide → HCID 54386710, compound

HRID 1704141Notes

Reaction equation

HRID 1704141 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.CS(O[CH2:18][CH:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)[CH3:20])(=O)=O.[Br:29]N1C(=O)CCC1=O.Br>CN(C)C(=O)C.C(Cl)(Cl)(Cl)Cl>[Br:29][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:18][CH:19]([O:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH3:20])=[CH:7][CH:6]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 67184N-bromobutanimideHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 20378389HCID 20378389, compound

Product 1

HCID 54386710HCID 54386710, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 31374DimethylacetamideSolvent

Procedure

As described in Example 68, 46 g of methyl p-hydroxyphenylacetate is reacted with 2-(p-Fluorophenoxy)-1-propanol O-methane-sulfonate in 400 ml of N,N-dimethylacetamide at 100° C. for 18 hrs. The product is dissolved in 1250 ml of carbon tetrachloride and N-bromosuccinimide added. Anhydrous HBr is added and the mixture is stirred and refluxed for 24 hrs. The mixture is filtered through a short column of silica gel and the solvent removed to give the product as a viscous oil.

Workup

  1. temperaturerefluxed for 24 hrs
  2. filtrationThe mixture is filtered through a short column of silica gel
  3. customthe solvent removed

Sources & evidence

ORD record
ord-4f210e7120ed47c9addc43265f87b0d2
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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