Hydrogen Bromide → HCID 86613566, compound

HRID 2219418Notes

Reaction equation

HRID 2219418 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13](Cl)=[O:14])=[C:11]([CH2:16][O:17][CH3:18])[O:10][N:9]=2)=[CH:4][CH:3]=1.[N+](=[CH2:21])=[N-].[BrH:22]>C(Cl)Cl.CCOCC>[Br:22][CH2:21][C:13]([C:12]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:9][O:10][C:11]=1[CH2:16][O:17][CH3:18])=[O:14]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 9550DiazomethaneHCID 87393347HCID 87393347, compound

Product 1

HCID 86613566HCID 86613566, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(4-fluoro-phenyl)-5-methoxyrnethyl-isoxazole-4-carboxylic acid chloride (2.7 g, 10.0 mmol) in methylene chloride (50 mL) was added diazomethane solution in ether (0.1 N, 100 mL) at ice-bath cooling temperature. The reaction was stirred for 1.5 h at 0° C. and allowed to stand overnight in a freezer at 0° C. An aqueous solution of hydrobromic acid (>40 wt %, 70 mL) was added dropwise to the reaction solution at ice-bath cooling temperature. After complete addition, the resulting mixture was stirred at 0° C. for 0.5 h and then allowed to warm up to room temperature and stirred for 1.5 h. The organic layer was separated, and the aqueous phase was extracted with ether. The combined ether solution was then washed with water and brine, dried over sodium sulphate and evaporated to afford the crude title compound (3.8 g) which was obtained as a light yellow liquid. MS: m/e=328.0/330.4 [M+H]+.

Workup

  1. temperaturecooling temperature
  2. waitto stand overnight in a freezer at 0° C
  3. temperaturecooling temperature
  4. additionAfter complete addition
  5. stirringthe resulting mixture was stirred at 0° C. for 0.5 h
  6. temperatureto warm up to room temperature
  7. stirringstirred for 1.5 h
  8. customThe organic layer was separated
  9. extractionthe aqueous phase was extracted with ether
  10. washThe combined ether solution was then washed with water and brine
  11. dry with materialdried over sodium sulphate
  12. customevaporated

Sources & evidence

ORD record
ord-fceb3a37313b48299315f6972caf2f2b
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

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