Cesium carbonate → 1-[3-(Bromomethyl)benzyl]-3-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

HRID 1818821Notes

Reaction equation

HRID 1818821 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][S:9]1(=[O:18])=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+].[Br:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33]Br)[CH:28]=1>>[Br:25][CH2:26][C:27]1[CH:28]=[C:29]([CH:30]=[CH:31][CH:32]=1)[CH2:33][N:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[S:9]1(=[O:18])=[O:17]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 69373Benzene, 1,3-bis(bromomethyl)-HCID 468330941-(2-Fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

Product 1

HCID 687116231-[3-(Bromomethyl)benzyl]-3-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxideYield 70%

Procedure

In an analogous manner to general procedure IV, 1-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole2,2-dioxide (0.20 g, 0.75 mmol) was treated with cesium carbonate (0.24 g, 0.75 mmol) and 1,3-bis(bromomethyl)benzene) (0.80 g, 3.00 mmol) to provide 0.23 g (70%) of 1-[3-(bromomethyl)benzyl]-3-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole2,2-dioxide. MS (ES) m/z 446.7; HPLC purity 98.5% at 210-370 nm, 10.8 min.; Xterra RP18, 3.5 u, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. Ph=3.5/ACN+MeOH) for 10 min, hold 4 min

Sources & evidence

ORD record
ord-34e7deb2967942c6af05f5bdc9125ce0
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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