Sulfuric Acid → 2-Bromo-4-methylpentanoic acid

HRID 1249342Notes

Reaction equation

HRID 1249342 reaction equation
N[C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].S(=O)(=O)(O)O.[Br-:15].[K+].N([O-])=O.[Na+]>>[Br:15][CH:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[C:7]([OH:9])=[O:8]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 253877Potassium BromideHCID 439524D-LeucineHCID 23668193Sodium Nitrite

Product 1

HCID 1426812-Bromo-4-methylpentanoic acid

Conditions

Temperature
0 °C

Procedure

A total of 50 g. of D-Leu are taken up in 1200 ml. of 2.5 N sulfuric acid containing 250 g. of potassium bromide. The mixture is cooled to 0° C. and stirred while adding 65.5 g. of sodium nitrite in small portions over a period of 11/2 hours. The solution is stirred for an additional hour at 0° C., and then heated to 25° C. and stirred another hour. The mixture is extracted with ether, the ether layer separated, washed with water, and dried over anhydrous sodium sulfate to give the desired product.

Workup

  1. additionwhile adding 65.5 g
  2. stirringThe solution is stirred for an additional hour at 0° C.
  3. temperatureheated to 25° C.
  4. stirringstirred another hour
  5. extractionThe mixture is extracted with ether
  6. customthe ether layer separated
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-5ab0505eec8242eb942d93a3654219e5
Source dataset
uspto-grants-1986_12
Patent number
US04631270

Reaction notes

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