Reaction #1425

Reaction equation

Potassium bromide

D-norleucine

sodium nitrite

→

crude title product

(S)-2-Bromohexanoic acid

Solvents

sulfuric acid

Conditions

Workup

1. 1
   Temperaturemaintaining the temperature between -10° and -5° C
2. 2
   workup.ADDITIONAfter addition
3. 3
   Otherthe foamy reaction
4. 4
   Temperaturewarmed to room temperature
5. 5
   workup.STIRRINGstirred for another hour
6. 6
   ExtractionThe reaction mixture was then extracted twice with ether
7. 7
   Washthe ether extracts were washed once with water
8. 8
   Dryingdried (magnesium sulfate)
9. 9
   Filtrationfiltered
10. 10
    Otherevaporated
11. 11
    Otherto give 3.3 g

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.

Source