Hydrogen Bromide → HCID 68828061, compound

HRID 1453964Notes

Reaction equation

HRID 1453964 reaction equation
[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18]C)[CH:13]=3)[C:4]([CH3:20])([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3]1.Br.[OH-].[Na+]>C(O)(=O)C>[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=3)[C:4]([CH3:20])([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 68828065HCID 68828065, compound

Product 1

HCID 68828061HCID 68828061, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a 25 mL single-necked flask was added 180 mg (0.65 mmol) of 9 and 5 mL of glacial acetic acid and 5 mL of 48% HBr. This mixture was heated under reflux for 18 h and then cooled to room temperature. The pH was then adjusted to 10 with cooling with 50% NaOH. This mixture was extracted 3× with methylene chloride. The organic extracts were dried (Na2SO4), and concentrated under reduced pressure to give 0.17 g (99%) of crude product as a white solid. Purification by chromatography on alumina using 15% ethyl acetate/hexane gave 0.140 g (83%) of desired product as a crystalline white solid.

Workup

  1. temperatureThis mixture was heated
  2. temperatureunder reflux for 18 h
  3. extractionThis mixture was extracted 3× with methylene chloride
  4. dry with materialThe organic extracts were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customto give 0.17 g (99%) of crude product as a white solid
  7. customPurification by chromatography on alumina using 15% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d7486e5b227f4ba480ea1dd5c31eee46
Source dataset
uspto-grants-2009_01
Patent number
US07476679B2

Reaction notes

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