Hydrogen Bromide → HCID 19086905, compound

HRID 2253956Notes

Reaction equation

HRID 2253956 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:22]=[CH:21][C:19](N)=[CH:18][CH:17]=1.[BrH:23].N([O-])=O.[Na+].[C:28]([O:32][CH2:33][CH3:34])(=[O:31])[CH:29]=[CH2:30]>CC(C)=O.CO.O>[Br:23][CH:29]([CH2:30][C:19]1[CH:21]=[CH:22][C:16]([O:15][CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:6][C:2]=2[CH3:1])=[CH:17][CH:18]=1)[C:28]([O:32][CH2:33][CH3:34])=[O:31]

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 8821Ethyl AcrylateHCID 15026342HCID 15026342, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 19086905HCID 19086905, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
38 °C

Procedure

To a solution of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]aniline (U.S. Pat. No. 4,725,610) (3.7 g, 12.6 mmol) in acetone (50 ml) and methanol (50 ml), cooled to 0° C., was added 48% hydrobromic acid (6.2 ml, 54 mmol), and after 5 minutes a solution of sodium nitrite (1.0 g, 15 mmol) in water (5 ml), dropwise, keeping the temperature below 5° C. After 15 minutes ethyl acrylate (8.6 ml, 79 mmol) was added dropwise, the mixture was warmed to 38° C. and cuprous oxide (0.42 g, 2.9 mmol) was added. The solution was stirred 1 hour at 40° C., then concentrated, diluted with aqueous ammonia and extracted with ethyl acetate (3×30 ml). The combined extracts were washed with water (2×), brine, dried over magnesium sulfate and concentrated. The product, ethyl alpha-bromo-4-[2-(5 -methyl-2-phenyl-4-oxazolyl)ethoxy]benzenepropanoate, was isolated by flash chromatography (hexane/ethyl acetate, 4:1) as a yellow oil (1.17 g).

Workup

  1. customthe temperature below 5° C
  2. concentrationconcentrated
  3. additiondiluted with aqueous ammonia
  4. extractionextracted with ethyl acetate (3×30 ml)
  5. washThe combined extracts were washed with water (2×), brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-41361fdef6894348bf53bee8b092378a
Source dataset
uspto-grants-1993_08
Patent number
US05232945

Reaction notes

Loading…