2-fluoro-5-(2-methyl-[1,3]dioxolan-2-yl)-benzenesulfonamide → 5-(2-Bromomethyl-[1,3]dioxolan-2-yl)-2-fluoro-benzenesulfonamide

HRID 990599Notes

Reaction equation

HRID 990599 reaction equation
[Br-:1].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[F:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2([CH3:46])[O:45][CH2:44][CH2:43][O:42]2)=[CH:37][C:36]=1[S:47]([NH2:50])(=[O:49])=[O:48]>CC#N>[Br:1][CH2:46][C:41]1([C:38]2[CH:39]=[CH:40][C:35]([F:34])=[C:36]([S:47]([NH2:50])(=[O:49])=[O:48])[CH:37]=2)[O:45][CH2:44][CH2:43][O:42]1

Participants

4

Reactant 2

HCID 110216402-fluoro-5-(2-methyl-[1,3]dioxolan-2-yl)-benzenesulfonamideHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 110783135-(2-Bromomethyl-[1,3]dioxolan-2-yl)-2-fluoro-benzenesulfonamideYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 8.4 g (0.0225 mole) of phenyltrimethylammonium tribromide in 20 mL of CH3CN was added dropwise to a solution of 5.2 g (0.022 mole) 2-fluoro-5(2-methyl-[1,3]dioxolan-2-yl)-benzenesulfonamide III in 100 mL of CH3CN. The reaction was stirred at room temperature for 1 hr. The solvent was evaporated in vacuo. The residue was dissolved in EtOAc, washed with water, dried over Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel eluting with CH2Cl2/Et2O::9/1 to give 4.6 g of IV (62%) as an oil. CH2Cl2/Et2O::9/1 single-spot material Rƒ 0.30.1H NMR (300 MHz CDCl3) δ: (3.68, s, 2H), (3.80,m , 2H), (4.21, m, 2H), 5.15, broad s, 2H), (7.26, t, 1H), (7.75, m, 1H), 8.15, dd, 1H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel eluting with CH2Cl2/Et2O

Sources & evidence

ORD record
ord-8a3e9eafd05846499fd43910bc549e9c
Source dataset
uspto-grants-2002_10
Patent number
US06461822B2

Reaction notes

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