1,3-Dibromopropane → HCID 69967358, compound

HRID 2289105Notes

Reaction equation

HRID 2289105 reaction equation
[CH:1]1([CH2:4][C:5]2[C:13]3[O:12][N:11]=[C:10]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:9]=3[CH:8]=[CH:7][C:6]=2[OH:20])[CH2:3][CH2:2]1.[Br:21][CH2:22][CH2:23][CH2:24]Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH:1]1([CH2:4][C:5]2[C:13]3[O:12][N:11]=[C:10]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:9]=3[CH:8]=[CH:7][C:6]=2[O:20][CH2:24][CH2:23][CH2:22][Br:21])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 136333676HCID 136333676, compound

Product 1

HCID 69967358HCID 69967358, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 7-cyclopropylmethyl-3-phenyl-6-hydroxybenz-[4,5]-isoxazole (0.25 grams) in 2-butanone (3.0 mL) was treated with 1,3-dibromopropane (0.48 mL) and potassium carbonate (0.50 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 7-cyclopropylmethyl-3-phenyl-6-(3-bromopropyloxy)benz-[4,5]-isoxazole. A solution of 3-chloro-4-hydroxyphenylacetic acid methyl ester (42.0 mg) in DMF (1.0 mL) was treated with potassium carbonate (26 mg) and this mixture was stirred for 0.5 hours. Then 7-cyclopropylmethyl-3-phenyl-6-(3-bromopropyloxy)benz-[4,5]-isoxazole was added and the mixture was stirred over night. The reaction mixture was partitioned between ethyl acetate and 1 M HCl solution. The organic was dried over sodium sulfate and filtered. The solvent was removed in vacuo and the residue was chromatographed on silica gel using methlene chloride and hexane (1:1) to give an oil. A solution of methyl 3-chloro-4-(3-(3-phenyl-7-cyclopropylmethyl-6-benz-[4,5]-isoxazoloxy)-butyloxy)phenylacetic acid (0.04 grams) in methanol (1.5 mL) was treated with a solution of lithium hydroxide in water (1.01 M; 0.1 mL). The reaction was refluxed 1 hour. The reaction mixture was partitioned between isopropyl acetate and 0.1N HCl. The organic was dried over magnesium sulfate, filtered and concentrated to a solid. The solid was suspended in methylene chloride/cyclohexane (1:1; 2 mL). The mixture was refluxed briefly and cooled to 0° C. The title compound was isolated by filtration.

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-d5e9cc5ab47f4a89b00b63f44e062885
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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