Potassium Bromide → 2-Bromohexanoic acid, (S)-

HRID 2256446Notes

Reaction equation

HRID 2256446 reaction equation
[Br-:1].[K+].N[C@@H:4]([C:9]([OH:11])=[O:10])[CH2:5][CH2:6][CH2:7][CH3:8].N([O-])=O.[Na+]>S(=O)(=O)(O)O>[Br:1][C@@H:4]([CH2:5][CH2:6][CH2:7][CH3:8])[C:9]([OH:11])=[O:10]

Participants

5

Conditions

Temperature
-10 °C

Procedure

Potassium bromide (15.9 g., 133 mmol.) was added to a stirred solution of D-norleucine (5.0 g., 38 mmol.) in 2.5N sulfuric acid (77 ml.) at room temperature. The reaction mixture was cooled to -10° C. and solid sodium nitrite (3.94 g., 57 mmol.) was added portionwise, maintaining the temperature between -10° and -5° C. After addition was complete, the foamy reaction was stirred for 1 hour and then warmed to room temperature and stirred for another hour. The reaction mixture was then extracted twice with ether, the ether extracts were washed once with water, dried (magnesium sulfate), filtered and evaporated to give 3.3 g. of crude title product.

Workup

  1. temperaturemaintaining the temperature between -10° and -5° C
  2. additionAfter addition
  3. customthe foamy reaction
  4. temperaturewarmed to room temperature
  5. stirringstirred for another hour
  6. extractionThe reaction mixture was then extracted twice with ether
  7. washthe ether extracts were washed once with water
  8. dry with materialdried (magnesium sulfate)
  9. filtrationfiltered
  10. customevaporated
  11. customto give 3.3 g

Sources & evidence

ORD record
ord-24b3cf8ce6ce4797b8002a3a4e8a2759
Source dataset
uspto-grants-1997_08
Patent number
US05654294

Reaction notes

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