Hydrogen Bromide → (2R)-2-bromo-4-methylpentanoic acid

HRID 849732Notes

Reaction equation

HRID 849732 reaction equation
N[C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].N([O-])=O.[Na+].[BrH:14]>>[Br:14][C@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 439524D-LeucineHCID 23668193Sodium Nitrite

Product 1

HCID 12697060(2R)-2-bromo-4-methylpentanoic acid

Conditions

Temperature
0 °C

Procedure

To a solution of D-leucine (50 g, 0.381 mol) in 570 mL of 3N HBr (aq) at 0° C. was added sodium nitrite (42 g, 1.6 eq) portion-wise over 1 hour and 15 minutes. The reaction was further stirred for 3 hrs at 0° C. then it was extracted with ether (1000 mL). After washing the ether layer with water (2×500 mL) it was dried over MgSO4 and concentrated. The red syrup was then co-evaporated with chloroform (3×200 mL) to remove the color and then it was pumped to give (2R)-2-bromo-4-methylpentanoic acid, as a colorless oil with a constant weight of 71.3 g.

Workup

  1. custom15 minutes
  2. extractionit was extracted with ether (1000 mL)
  3. washAfter washing the ether layer with water (2×500 mL) it
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated
  6. customto remove the color

Sources & evidence

ORD record
ord-1fe137c3bcbb4599809ebcf41d4a7adb
Source dataset
uspto-grants-2000_01
Patent number
US06013792

Reaction notes

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