Boron tribromide → 3-(5-(4-Carbazol-9-ylphenyl)-1,3,4-oxadiazol-2-yl)phenol

HRID 2278462Notes

Reaction equation

HRID 2278462 reaction equation
[CH:1]1[C:13]2[N:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[O:21][C:22]([C:25]5[CH:30]=[CH:29][CH:28]=[C:27]([O:31]C)[CH:26]=5)=[N:23][N:24]=4)=[CH:16][CH:15]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br.C(=O)=O.CC(C)=O>ClCCl>[CH:10]1[C:11]2[N:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[O:21][C:22]([C:25]5[CH:26]=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=5)=[N:23][N:24]=4)=[CH:16][CH:15]=3)[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 25134Boron tribromide2×HCID 18522661Acetone cardiceHCID 675161502-(4-Carbazol-9-ylphenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole

Product 1

HCID 675161893-(5-(4-Carbazol-9-ylphenyl)-1,3,4-oxadiazol-2-yl)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-carbazol-9-ylphenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole (1.0 g, 2.40 mmol) in dichloromethane (10.0 ml) was dropwise added BBr3 (10.0 ml, 1M in dichloromethane) at −78° C. (dry-ice/acetone) under nitrogen. After addition of BBr3 solution, the reaction was taken to room temperature and kept at room temperature for 5 h. The reaction mixture was poured into ice-water (50.0 ml). Dichloromethane was evaporated under reduced pressure. The white solid was collected by filtration. After drying under vacuum, product as white solid was obtained in 0.97 g (100%) yield. 1H NMR (400 MHz, acetone-d6, δ): 8.91 (s, 1H, OH), 8.48 (m, 2H), 8.24 (dt, J1=8.0 Hz, J2=1.2 Hz, 2H), 7.91 (m, 2H), 7.71 (t, J=1.2 Hz, 1H), 7.69 (t, J=1.6 Hz, 1H), 7.56 (d, J=0.8 Hz, 1H), 7.54 (t, J=0.8 Hz, 1H), 7.46 (m, 3H), 7.32 (m, 2H), 7.12 (m, 111), 3.93 (s, 3H, OCH3). 13C NMR (100 MHz, acetone-d6, δ): 165.43, 164.72, 158.87, 141.48, 141.12, 131.44, 129.41, 128.23, 127.17, 126.04, 124.56, 123.65, 121.43, 121.26, 119.88, 118.89, 114.18, 110.62. MS-EI (m/z): [M]+ calcd for C26H17N3O2, 403.1. found 403.1.

Workup

  1. customat −78° C.
  2. customwas taken to room temperature
  3. customDichloromethane was evaporated under reduced pressure
  4. filtrationThe white solid was collected by filtration
  5. customAfter drying under vacuum
  6. customproduct as white solid was obtained in 0.97 g (100%)
  7. customyield

Sources & evidence

ORD record
ord-741108330c894eb897e25b9cb9f4e24c
Source dataset
uspto-grants-2015_09
Patent number
US09133177B2

Reaction notes

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