Hydrogen Bromide → HCID 23157961, compound

HRID 1360226Notes

Reaction equation

HRID 1360226 reaction equation
N([O-])=O.[Na+].[Br-:5].[K+].Br.N[CH:9]([CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[C:10]([OH:12])=[O:11]>O>[Br:5][CH:9]([CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[C:10]([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 253877Potassium BromideHCID 11506835HCID 11506835, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 23157961HCID 23157961, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At −5° C., sodium nitrite (176 mg) was slowly added to a solution of potassium bromide (591 mg) in a 0.75M aqueous hydrobromic acid solution and then 2-amino-5-(4-methoxyphenyl)pentanoic acid (300 mg) was added thereto. After stirring at the same temperature for 2 hours, the reaction mixture was poured into water (50 ml) and extracted with ethyl acetate (20 ml×twice). The organic layer was collected, washed with a saturated aqueous sodium chloride solution (30 ml), dried over sodium sulfate, and then concentrated under reduced pressure. 2-Bromo-5-(4-methoxyphenyl)pentanoic acid was obtained as 355 mg of a crude product.

Workup

  1. extractionextracted with ethyl acetate (20 ml×twice)
  2. customThe organic layer was collected
  3. washwashed with a saturated aqueous sodium chloride solution (30 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9babc469fa7941fd9932da02e7166c69
Source dataset
uspto-grants-2011_02
Patent number
US07879843B2

Reaction notes

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