Water → HCID 25254808, compound

HRID 2167331Notes

Reaction equation

HRID 2167331 reaction equation
C[O:2][C:3]1[CH:27]=[CH:26][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:18]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[O:16][N:15]=3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.O>C(Cl)Cl>[F:25][C:22]1[CH:21]=[CH:20][C:19]([C:17]2[O:16][N:15]=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([O:7][C:6]4[CH:26]=[CH:27][C:3]([OH:2])=[CH:4][CH:5]=4)=[CH:9][CH:10]=3)[N:18]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 25254648HCID 25254648, compound

Product 1

HCID 25254808HCID 25254808, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-(4-Methoxyphenoxy)phenyl)-5-(4-fluorophenyl)-1,2,4-oxadiazole (150 mg, 0.414 mmol) was suspended in dry methylene chloride (10.0 mL) and the mixture was placed under nitrogen and cooled to −80 C. Boron tribromide (1.0 M in CH2Cl2, 2.07 mmol) was added dropwise over 10 minutes. The mixture was allowed to warm to room temperature and stirred for 19 hours 30 minutes. The reaction mixture was then cooled to −80 C and H2O (2.0 mL) was added dropwise. The organic layer was removed under reduced pressure and the compound was purified by column chromatography (Hex/EtOAc 2:1) to give a white powder (144 mg, 100%). 1H NMR (500 MHz, DMSO-d6) δ(ppm): 6.83 (2H, d, J=8.8 Hz), 6.98 (2H, d, J=8.8 Hz), 7.04 (2H, t, J=8.8 Hz), 7.49 (2H, t, J=8.8 Hz), 8.03 (2H, d, J=9.0 Hz), 8.23 (2H, dd, J=8.8, 5.4 Hz), 9.49 (1H, s). 13C NMR (125 MHz, DMSO-d6) δ(ppm): 116.5 (CH), 116.9 (CH, d, J=22.5 Hz), 116.9 (CH), 119.7, 121.6 (CH, d, J=3.8 Hz), 121.7 (CH), 129.1, 130.8 (CH, d, J=10.0 Hz), 146.6, 154.5, 161.3, 164.9 (C, d, J=251.2 Hz), 167.8, 174.4. 19F (282 MHz, DMSO-d6) δ(ppm): −105.1-−105.2 (1F, m). MS (FAB+): 348 (MH+). HRMS for C20H13FN2O3 (MH+): calculated: 348.0910; found 348.0897.

Workup

  1. temperaturecooled to −80 C
  2. additionwas added dropwise
  3. customThe organic layer was removed under reduced pressure
  4. customthe compound was purified by column chromatography (Hex/EtOAc 2:1)

Sources & evidence

ORD record
ord-327b33c9b00d436f8bc195e73f31bff9
Source dataset
uspto-grants-2015_06
Patent number
US09045442B2

Reaction notes

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