Hydrogen Bromide → HCID 19358329, compound

HRID 1584822Notes

Reaction equation

HRID 1584822 reaction equation
[BrH:1].C([N:4]([CH2:7][CH3:8])[CH2:5][CH3:6])C.[C:9](Cl)([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].Cl>C(Cl)Cl.CCCCCC.O>[CH2:12]([O:11][C:9]([N:4]1[CH2:5][C:6]2[C:8](=[CH:12][CH:13]=[C:14]([Br:1])[CH:15]=2)[CH2:7]1)=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10387Benzyl chloroformate

Product 1

HCID 19358329HCID 19358329, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

In 25 ml of 47% hydrobromic acid was suspended 5.0 g of 2-(p-toluenesulfonyl)-5-bromoisoindoline, and 4.0 g of phenol and 15 ml of propionic acid were added to the suspension, after which the resulting mixture was heated under reflux for four hours. The reaction mixture was concentrated under reduced pressure, and ethanol was added to the residue obtained, after which the resulting crystals were collected by filtration, to obtain 3.5 g of 5-bromoisoindoline hydrobromide. The hydrobromide obtained was suspended in 50 ml of methylene chloride, and 2.8 g of triethylamine was added to the suspension, after which 2.4 g of carbobenzoxy chloride was dropwise added thereto with ice-cooling. Thereafter, the resulting mixture was stirred at room temperature for one hour. The reaction mixture was added 50 ml of water and the pH was adjusted to 1 with 6N hydrochloric acid. Thereafter, the organic layer formed was separated, washed with a saturated saline solution and then dried over anhydrous magnesium chloride. The solvent was then removed by distillation under reduced pressure. To the residue thus obtained was added n-hexane, and the resulting crystals were collected by filtration to obtain 3.8 g of colorless, crystalline 2-benzyloxycarbonyl-5-bromoisoindoline.

Workup

  1. temperaturewith ice-cooling
  2. customThereafter, the organic layer formed
  3. customwas separated
  4. washwashed with a saturated saline solution
  5. dry with materialdried over anhydrous magnesium chloride
  6. customThe solvent was then removed by distillation under reduced pressure
  7. customTo the residue thus obtained
  8. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-4295583a451046708e1ad16c69cbac91
Source dataset
uspto-grants-1999_08
Patent number
US05935952

Reaction notes

Loading…