Boron tribromide → HCID 71139195, compound

HRID 539523Notes

Reaction equation

HRID 539523 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=[S: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=[S:20])=[CH:21][CH:22]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 71139600HCID 71139600, compound

Product 1

HCID 71139195HCID 71139195, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Reaction of 147i (0.08 g, 0.25 mmol) with 1M BBr3 (0.38 mL) in dry CH2Cl2 (5 mL) within 48 h according to procedure 148a afforded pure 149i (65 mg, 88%) as olive green color solid. 1H NMR (400 MHz, CDCl3) δ 8.65 (d, J=5.3 Hz, 2H), 8.55 (s, 1H), 7.62 (d, J=8.0 Hz, 2H), 7.42 (m, 5H), 6.99 (d, J=7.5 Hz, 1H), 6.67 (t, J=7.0 Hz, 1H), 5.85 (s, 2H). 13C NMR (100 MHz, CDCl3) δ 170.05, 155.32, 150.25, 147.44, 138.22, 135.48, 130.91, 128.80, 127.55, 121.48, 113.73, 111.94, 59.91. HRMS (EI) calcd for C17H14N2OS [M]+ 294.0827. found 294.0823.

Sources & evidence

ORD record
ord-f28a15a35f16454f9b15535ff91045b4
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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