Boron tribromide → HCID 135430905, compound

HRID 1263572Notes

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

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

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

Sources & evidence

ORD record: ord-f484ce9286b44e22922c2fb5eedece2a
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06541490B1

Reaction notes

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