Boron tribromide → 4-(2-Chloro-6-fluorobenzyl)-2-(4-hydroxy-3,5-di methyl phenyl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide

HRID 1772956Notes

Reaction equation

HRID 1772956 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:3]=1[CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:8](=[O:16])(=[O:15])[N:7]([C:17]2[CH:22]=[C:21]([CH3:23])[C:20]([O:24]C)=[C:19]([CH3:26])[CH:18]=2)[C:6]1=[O:27].B(Br)(Br)Br.OC1C(C)=CC(N2C(=O)N(CC3C(F)=CC(F)=CC=3F)C3C=CC=CC=3S2(=O)=O)=CC=1C>>[Cl:1][C:2]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:3]=1[CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:8](=[O:15])(=[O:16])[N:7]([C:17]2[CH:18]=[C:19]([CH3:26])[C:20]([OH:24])=[C:21]([CH3:23])[CH:22]=2)[C:6]1=[O:27]

Participants

4

Reactant 3

HCID 25134Boron tribromideHCID 727212754-(2-Chloro-6-fluorobenzyl)-2-(4-methoxy-3,5-dimethylphenyl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxideHCID 727218952-(4-Hydroxy-3,5-dimethylphenyl)-4-(2,4,6-trifluorobenzyl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide

Product 1

HCID 727219884-(2-Chloro-6-fluorobenzyl)-2-(4-hydroxy-3,5-di methyl phenyl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxideYield 54.2%

Procedure

The title compound (0.12 g, 0.26 mmol) was prepared from (81) (0.23 g, 0.48 mmol) and boron tribromide (1.0M solution in DCM, 0.60 mL, 0.60 mmol) using the methods of (114).

Sources & evidence

ORD record
ord-dfb982258ce642ada7b089db16857294
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

Loading…