Boron tribromide → HCID 71139070, compound

HRID 539522Notes

Reaction equation

HRID 539522 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:22]=[CH:21][C:10]([CH2:11][N:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18]C)[C:13]3=[O:20])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.B(Br)(Br)Br>C(Cl)Cl>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][N:12]3[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[C:13]3=[O:20])=[CH:21][CH:22]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 71138807HCID 71138807, compound

Product 1

HCID 71139070HCID 71139070, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Reaction of 146i (0.10 g, 0.34 mmol) with 1M BBr3 (0.51 mL) in dry CH2Cl2 within 48 h according to procedure 148a afforded pure 148i (79 mg, 83%) as slightly brownish solid. 1H NMR (400 MHz, CDCl3) δ 8.65 (s, 2H), 7.46 (s, 2H), 7.39 (d, J=7.9 Hz, 2H), 6.83 (dd, J=22.5, 7.0 Hz, 2H), 6.16 (t, J=7.0 Hz, 1H), 5.22 (s, 2H). 13C NMR (100 MHz, CDCl3) δ 150.23, 147.62, 146.76, 137.98, 136.87, 128.66, 127.51, 126.64, 121.58, 113.66, 107.13, 52.19. HRMS (FAB) calcd for C17H15N2O2 [M+H]+ 279.1133. found 279.1147.

Sources & evidence

ORD record
ord-e8e64aa17be84dfeae64295d11152187
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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