Acetic Acid → HCID 86626432, compound

HRID 1520409Notes

Reaction equation

HRID 1520409 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH2:10][OH:11].C(O)(=O)C.[Cl:16][C:17]1[CH:22]=[C:21]([C:23]([C:25]([F:28])([F:27])[F:26])=[CH2:24])[CH:20]=[C:19]([Cl:29])[CH:18]=1.Cl[O-].[Na+]>C(O)C.C(OCC)(=O)C.O1CCCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]2[CH2:24][C:23]([C:21]3[CH:22]=[C:17]([Cl:16])[CH:18]=[C:19]([Cl:29])[CH:20]=3)([C:25]([F:26])([F:27])[F:28])[O:11][N:10]=2)=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 787HydroxylamineHCID 707414-BromobenzaldehydeHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene2×HCID 23665760Sodium Hypochlorite

Product 1

HCID 86626432HCID 86626432, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromobenzaldehyde (3.70 g, 20 mmol) in ethanol (30 mL) was added 50% aqueous hydroxylamine (1.25 mL, 21 mmol) and glacial acetic acid (1.25 mL, 21 mmol). After 30 minutes, the reaction mixture was diluted with ethyl acetate and washed with water and with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated to leave a white solid. To a solution of this solid in tetrahydrofuran (80 mL) and 1,3-dichloro-5-[1-(trifluoromethyl)ethenyl]benzene (i.e. the product from Example 1, Step A) (4.82 g, 20 mmol) was added an aqueous solution of sodium hypochlorite (6.15%—Clorox® brand) (80 mL) dropwise over 1 h. The reaction mixture was stirred at ambient temperature for 16 h. The phases were separated, and the aqueous phase was extracted once with diethyl ether. The combined organic phases were washed with saturated aqueous sodium bisulfite solution and saturated aqueous sodium chloride solution, and dried over magnesium sulfate, and concentrated to leave a white solid. This solid was triturated with warm (40° C.) hexanes, allowed to cool, and solids were collected on a glass frit and dried to obtain the title product as a white solid (5.25 g).

Workup

  1. washwashed with water and with saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customto leave a white solid
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted once with diethyl ether
  7. washThe combined organic phases were washed with saturated aqueous sodium bisulfite solution and saturated aqueous sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customto leave a white solid
  11. customThis solid was triturated
  12. temperaturewith warm (40° C.) hexanes
  13. temperatureto cool
  14. customsolids were collected on a glass frit
  15. customdried

Sources & evidence

ORD record
ord-a70d2b1f2b1d4c749f7b3ff2de706c18
Source dataset
uspto-grants-2015_07
Patent number
US09073910B2

Reaction notes

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