Sulfuric Acid → 3-(Benzyloxy)-2-bromopropanoic acid

HRID 1943141Notes

Reaction equation

HRID 1943141 reaction equation
[C:1]1([CH2:7][O:8][CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-:15].[K+].OS(O)(=O)=O.N([O-])=O.[Na+]>O>[Br:15][CH:10]([CH2:9][O:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:12]([OH:14])=[O:13]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 78457O-benzyl-L-serineHCID 253877Potassium BromideHCID 23668193Sodium Nitrite

Product 1

HCID 109562653-(Benzyloxy)-2-bromopropanoic acidYield 90.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Racemic O-(phenylmethyl)serine (5 g, 25.6 mmol) and potassium bromide (10.7 g, 89.6 mmol) were dissolved in ice-cooled H2SO4 (2.5N) and treated with an solution of sodium nitrite (2.65 g) in water (30 ml) over 50 minutes (keeping the reaction temperature <4° C.). The reaction was then stirred at 0° C. for 45 minutes and then at rt for 1 h, extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with water, brine, dried (MgSO4), filtered and evaporated to give the product as a yellow oil (6 g, 90%).

Workup

  1. customthe reaction temperature <4° C.
  2. waitat rt for 1 h
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. washThe combined organic extracts were washed with water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c8fe1428c359483d896c7ebc1030f529
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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