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

HRID 132983

Reaction equation

HRID 132983 reaction equation
N[C@@H:2]([CH2:6][CH2:7][CH2:8][CH3:9])[C:3]([OH:5])=[O:4].[BrH:10].N([O-])=O.[Na+]>O>[Br:10][C@@H:2]([CH2:6][CH2:7][CH2:8][CH3:9])[C:3]([OH:5])=[O:4]

Participants

5

Procedure

(S)-2-aminohexanoic acid (FW 131.2, also known as L-norleucine) (1 g, 7.62 mmol), which is commercially available from Sigma Chemical Co at Sigmaaldrich.com, is dissolved in a mixture of HBr 48% (7.0 mL, 61 mmol) and H2O (10 mL). At 0° C., a solution of NaNO2 (1.7 g, 24 mmol) in H2O (5 mL) is added over a period of 30 min. The reaction is stirred for two hours. The reaction mixture is degassed in vacuo and extracted with EtOAc (2×20 mL). The extracts are washed with water (15 mL), dried (Na2SO4), filtered and evaporated to give (S)-2-bromohexanoic acid.

Workup

  1. customThe reaction mixture is degassed in vacuo
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe extracts are washed with water (15 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c80dfe6010ea41a0adda434b542efe92
Source dataset
uspto-grants-2008_06
Patent number
US07390789B2

Linked notes

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