Boron tribromide → HCID 15285937, compound

HRID 260061Notes

Reaction equation

HRID 260061 reaction equation
[F:1][C:2]([F:24])([F:23])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][CH2:20][O:21]C)[N:14]=2)=[CH:9][CH:8]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[F:24][C:2]([F:1])([F:23])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][CH2:20][OH:21])[N:14]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 9884600HCID 9884600, compound

Product 1

HCID 15285937HCID 15285937, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.70 g of 5-[4-(4,4,4-trifluorobutoxy)phenyl]-3-methoxyethyl-1,3,4-oxadiazol-2(3H)-one in 10 ml of dichloromethane are added dropwise 1.2 g of boron tribromide. The mixture is left to react overnight and is then treated with aqueous sodium bicarbonate solution and extracted with dichloromethane. The organic phase is washed with water, dried over sodium sulphate and concentrated. The crude product obtained is purified on a column of silica with a 1/1 mixture of ethyl acetate and heptane. 200 mg of product are obtained.

Workup

  1. waitThe mixture is left
  2. customto react overnight
  3. extractionextracted with dichloromethane
  4. washThe organic phase is washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customThe crude product obtained
  8. customis purified on a column of silica with a 1/1 mixture of ethyl acetate and heptane

Sources & evidence

ORD record
ord-8a4e22a1c95d4c00aee001164ad8822c
Source dataset
uspto-grants-1996_06
Patent number
US05525619

Reaction notes

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