HCID 23336680, compound → HCID 23336676, compound

HRID 903577Notes

Reaction equation

HRID 903577 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[C:9]3[C:18](=[O:19])[CH:17]=[C:16]([C:20]([O:22]CC)=[O:21])[S:15][C:10]3=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5][C:4]([C:25]([O:27]CC)=[O:26])=[CH:3]1>C(O)(=O)C.Br>[O:1]=[C:2]1[C:7]2[CH:8]=[C:9]3[C:18](=[O:19])[CH:17]=[C:16]([C:20]([OH:22])=[O:21])[S:15][C:10]3=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5][C:4]([C:25]([OH:27])=[O:26])=[CH:3]1

Participants

4

Reactant 1

HCID 23336680HCID 23336680, compound

Product 1

HCID 23336676HCID 23336676, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent2×

Procedure

The product of step (g) (2.7 g) in glacial acetic acid (100 mls) and 48% aqueous hydrobromic acid (6 mls) was heated under reflux for 4 hours. More aqueous hydrobromic acid (3 mls) was added and refluxing continued overnight. The reaction was allowed to cool and the precipitated solid was collected by filtration, washed with ether and dried in vacuo at 80° C. for 3 hours to give 2.0 g of the desired product, mp 308°-310° dec.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperaturerefluxing continued overnight
  3. temperatureto cool
  4. filtrationthe precipitated solid was collected by filtration
  5. washwashed with ether
  6. customdried in vacuo at 80° C. for 3 hours

Sources & evidence

ORD record
ord-7199a2d9561545b6a94e53baa7d3f97e
Source dataset
uspto-grants-1980_10
Patent number
US04228173

Reaction notes

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