Hydrogen Bromide → HCID 86613563, compound

HRID 2219410Notes

Reaction equation

HRID 2219410 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[O:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]=1[C:15](Cl)=[O:16].[N+](=[CH2:20])=[N-].[BrH:21]>CCOCC>[Br:21][CH2:20][C:15]([C:5]1[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:7][O:8][C:4]=1[CH2:3][O:2][CH3:1])=[O:16]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 9550DiazomethaneHCID 87392931HCID 87392931, compound

Product 1

HCID 86613563HCID 86613563, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 5-methoxymethyl-3-phenyl-isoxazole-4-carboxylic acid chloride (11.16 g, 44 mmol) in dry ether (350 mL) was added diazomethane solution in ether (0.1 N, 100 mL) at iced-bath cooling temperature. The reaction was stirred for 2 h at 0° C. Aqueous solution of hydrobromic acid (>40 wt %, 100 mL) was then added dropwise to the reaction solution at iced-bath cooling temperature. After complete addition, the organic layer was separated, and the aqueous phase was extracted with ether. The combined ether solution was washed with water and brine, dried over magnesium sulphate and evaporated to afford the title compound (12.83 g, 94%) which was obtained as a light yellow liquid. MS: m/e=310.0/311.9 [M+H]+.

Workup

  1. temperaturecooling temperature
  2. temperaturecooling temperature
  3. additionAfter complete addition
  4. customthe organic layer was separated
  5. extractionthe aqueous phase was extracted with ether
  6. washThe combined ether solution was washed with water and brine
  7. dry with materialdried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-eb9b6370b3cf4a50b644d3058d98606e
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

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