Boron tribromide → HCID 58941786, compound

HRID 2097652Notes

Reaction equation

HRID 2097652 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[O:12][N:11]=[C:10]2[C:15]2[C:19]([CH2:20][CH2:21][O:22]C)=[N:18][O:17][N:16]=2)[CH:5]=[CH:6][C:7]=1[F:8].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[O:12][N:11]=[C:10]2[C:15]2[C:19]([CH2:20][CH2:21][OH:22])=[N:18][O:17][N:16]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58941893HCID 58941893, compound

Product 1

HCID 58941786HCID 58941786, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(3-chloro-4-fluorophenyl)-3-[4-(2-methoxyethyl)-1,2,5-oxadiazol-3-yl]-1,2,4-oxadiazol-5(4H)-one (2.55 g, 0.00748 mol) in DCM (24 mL) was added 1.0 M of boron tribromide in DCM (22.4 mL) under an atmosphere of nitrogen at −78° C. The reaction solution was allowed to warm to rt over 2.5 h. The reaction was quenched with saturated NaHCO3 at 0° C. and diluted with ethyl acetate. The aqueous layer was extracted with ethyl acetate once, the combined organic solutions were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (60% ethyl acetate/hexane) to give the desired product as an off white solid (2.3 g, 96%). MF═C12H8ClFN4O4; LCMS calculated for C12H9ClFN4O4(M+H)+: m/z=327.0.

Workup

  1. customThe reaction was quenched with saturated NaHCO3 at 0° C.
  2. additiondiluted with ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate once
  4. dry with materialthe combined organic solutions were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel chromatography (60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-db5c8e4cffc2473a999c7d4594c5f8aa
Source dataset
uspto-grants-2013_05
Patent number
US08450351B2

Reaction notes

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