Boron tribromide → HCID 135430905, compound

HRID 566917Notes

Reaction equation

HRID 566917 reaction equation
[OH:1][C:2]1[C:7]([O:8]C)=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]1[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28]C)[C:23]=3[OH:30])[N:17]=2)[CH:13]=[CH:12][CH:11]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:30][C:23]1[C:24]([OH:28])=[CH:25][CH:26]=[CH:27][C:22]=1[C:18]1[N:17]=[C:16]([C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([OH:8])[C:2]=3[OH:1])[N:15]=2)[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 135544181HCID 135544181, compound

Product 1

HCID 135430905HCID 135430905, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 6,6′-bis(2-hydroxy-3-methoxyphenyl)-2,2′-bipyridine (2.03 g, 50.8 mmol) dissolved in DCM (25 ml) was added boron tribromide (1M in DCM, 40.6 ml, 40.6 mmol) and the reaction stirred for 48 hours. The reaction was cooled to 0° C. and quenched by dropwise addition of methanol. The solvent was evaporated under vacuum to give the title compound as a yellow solid (100%); δH [2H6]-DMSO 8.30,(2H, d), 8.22,(2H, t), 8.10,(2H, d), 7.53,(2H, d), 6.88,(2H, d), 6.78,(2H, t).

Workup

  1. customquenched by dropwise addition of methanol
  2. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-69d9f067799c4abe9b0084d9441e4aa8
Source dataset
uspto-grants-2001_01
Patent number
US06177419B1

Reaction notes

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