Boron tribromide → HCID 22339931, compound

HRID 539516Notes

Reaction equation

HRID 539516 reaction equation
[CH2:1]([N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14]C)[C:9]1=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[C:9]1=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 71139868HCID 71139868, compound

Product 1

HCID 22339931HCID 22339931, compoundYield 117.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Reaction of 141b (0.15 g, 0.55 mmol) with 1M BBr3 (0.66 mL) in dry CH2Cl2 (5 mL) within 48 h according to procedure 142a afforded pure 142b (0.13 g, 90%) as slightly brownish solid. 1H NMR (400 MHz, CDCl3) δ 7.3.1 (m, 5H), 6.83 (m, 3H), 6.14 (t, J=7.1 Hz, 1H), 5.19 (s, 2H). 13C NMR (100 MHz, CDCl3) δ 158.62, 146.78, 135.82, 128.74, 127.97, 126.53, 113.94, 106.95, 52.18. HRMS (EI) calcd for C12H11NO2 [M]+ 201.0792. found 201.0790.

Sources & evidence

ORD record
ord-3d566395ee3d44bc9e7422eff40e8785
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

Loading…