Sulfuric Acid → 2-Bromo-4,4-dimethylpentanoic acid
Reaction equation
N[C@H:2]([CH2:6][C:7]([CH3:10])([CH3:9])[CH3:8])[C:3]([OH:5])=[O:4].S(=O)(=O)(O)O.[Br-:16].[K+].N([O-])=O.[Na+]>O>[Br:16][CH:2]([CH2:6][C:7]([CH3:10])([CH3:9])[CH3:8])[C:3]([OH:5])=[O:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of (R)-2-amino-4,4-dimethylpentanoic acid (950 mg, 6.55 mmol) in 2.5N aqueous sulfuric acid (13 ml, 33 mmol) was cooled to -5° C. and treated with potassium bromide (2.72 g, 22.9 mmol) in one portion. The colorless solution was treated with sodium nitrite (680 mg, 9.86 mmol) portionwise, keeping the temperature between 0° and 3° C. over a period of 25 minutes. The reaction mixture was stirred at 0° C. for one hour and at room temperature for 1.5 hours. The reaction mixture was poured into water (10 ml). The product was extracted with ether (60 ml), washed with water (20 ml) and brine (20 ml), dried (magnesium sulfate), and concentrated in vacuo to give the title product as a colorless liquid.
Workup
- customthe temperature between 0° and 3° C.
- customof 25 minutes
- extractionThe product was extracted with ether (60 ml)
- washwashed with water (20 ml) and brine (20 ml)
- dry with materialdried (magnesium sulfate)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-6721c8d229ba43a59a34d2dade673432
- Source dataset
- uspto-grants-1996_04
- Patent number
- US05508272
Reaction notes
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