1,3-Dibromopropane → HCID 12031259, compound

HRID 2289097Notes

Reaction equation

HRID 2289097 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[C:7]2[CH:8]=[CH:9][C:10]([OH:15])=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5][N:4]=1.[Br:18][CH2:19][CH2:20][CH2:21]Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[F:17][C:2]([F:1])([F:16])[C:3]1[C:7]2[CH:8]=[CH:9][C:10]([O:15][CH2:21][CH2:20][CH2:19][Br:18])=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5][N:4]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 1358008127-Propyl-3-(trifluoromethyl)benzo[d]isoxazol-6-ol

Product 1

HCID 12031259HCID 12031259, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 3-trifluoromethyl-7-propyl-6-hydroxybenzisoxazole (2.5 grams) in 2-butanone (30 mL) was treated with 1,3-dibromopropane (4.8 mL) and potassium carbonate (5.0 grams). The mixture was refluxed for 4 hours. The reaction mixture was partitioned between isopropyl acetate and pH 4 buffer. The organic was washed once with water, then dried over magnesium sulfate. The organic was filtered and evaporated to an oil which was flitered through a silica gel plug using methylene chloride and hexane (1:2) to give 3-trifluoromethyl-7-propyl-6-(3-bromopropyloxy)-benzisoxazole. A solution of 3-chloro-4-dimethylcarbamoylthio-phenylacetic acid methyl ester (0.33 grams) in dry methanol (3.5 mL) was treated with a solution of sodium methoxide in methanol (25 wt %; 0.341 mL). The solution was refluxed for 2 hours. HPLC analysis showed the disappearance of the carbamate. The solution was allowed to cool to 50° C. 3-trifluoromethyl-7-propyl-6-(3-bromopropyloxy)-benzisoxazole (0.31 grams) was added and the solution stirred for 1 hour. The reaction was partitioned between isopropyl acetate and pH 4 buffer. The organic was washed once more with pH 4 buffer, then water. The organic was dried over magnesium sulfate, filtered and concentrated to an oil. The oil was applied to a silica gel column packed with hexane/methylene chloride (2:1). The column was eluted with this mobile phase until the product began to appear in the eluant. The mobile phase was switched to 100% methylene chloride and elution continued until all the product was recovered.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. customThe reaction mixture was partitioned between isopropyl acetate and pH 4 buffer
  3. washThe organic was washed once with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe organic was filtered
  6. customevaporated to an oil which

Sources & evidence

ORD record
ord-507bb15c8dcc4706aafc54a450993da2
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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