Water → HCID 136003665, compound

HRID 415626Notes

Reaction equation

HRID 415626 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[C:11]([O:12][CH2:13][C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=3)[N:15]=2)=[CH:10][CH:9]=[C:8]([F:27])[C:7]=1[C:28]([NH2:30])=[O:29].O>C(Cl)Cl>[F:5][C:6]1[C:11]([O:12][CH2:13][C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[N:15]=2)=[CH:10][CH:9]=[C:8]([F:27])[C:7]=1[C:28]([NH2:30])=[O:29]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 59402683HCID 59402683, compound

Product 1

HCID 136003665HCID 136003665, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(Method L) Boron tribromide solution (1.0 M in CH2Cl2, 1.5 ml, 1.5 mmol, 2 equiv.) was added slowly, dropwise to stirred suspension of 2,6-difluoro-3-[3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl]methoxybenzenecarboxamide (272 mg, 0.75 mmol, 1 equiv.) in CH2Cl2 (5 ml), at r.t., under N2. The reaction mixture was stirred at r.t. for 4 h and poured into water (20 ml). CH2Cl2 (10 ml) was added and the biphasic mixture was stirred for 30 min. at r.t. The white un-dissolved solid was filtered, washed with water and Et2O, to give 170 mg (65% yield), mp 209-210° C., HPLC-MS (method 1): m/z 348 [M+H]+, Rt=3.00 min.

Workup

  1. customat r.t.
  2. stirringThe reaction mixture was stirred at r.t. for 4 h
  3. stirringthe biphasic mixture was stirred for 30 min. at r.t
  4. dissolutionThe white un-dissolved solid
  5. filtrationwas filtered
  6. washwashed with water and Et2O
  7. customto give 170 mg (65% yield), mp 209-210° C., HPLC-MS (method 1)

Sources & evidence

ORD record
ord-82d6f40d12494b1a84531e80250c4b4c
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

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