Sodium hydride → diisopropyl 1-bromo-2-[2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorophenyl]vinylphosphonate

HRID 566612Notes

Reaction equation

HRID 566612 reaction equation
[Br:1][CH:2]([P:13]([O:19][CH:20]([CH3:22])[CH3:21])(=[O:18])[O:14][CH:15]([CH3:17])[CH3:16])P(OC(C)C)(=O)OC(C)C.[H-].[Na+].[Cl:25][C:26]1[CH:33]=[C:32]([F:34])[C:31]([C:35]2[C:39]([Cl:40])=[C:38]([O:41][CH:42]([F:44])[F:43])[N:37]([CH3:45])[N:36]=2)=[CH:30][C:27]=1[CH:28]=O>>[Br:1][C:2]([P:13](=[O:18])([O:14][CH:15]([CH3:16])[CH3:17])[O:19][CH:20]([CH3:21])[CH3:22])=[CH:28][C:27]1[CH:30]=[C:31]([C:35]2[C:39]([Cl:40])=[C:38]([O:41][CH:42]([F:43])[F:44])[N:37]([CH3:45])[N:36]=2)[C:32]([F:34])=[CH:33][C:26]=1[Cl:25]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 118099222-Chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorobenzaldehydeHCID 13479865Tetrapropan-2-yl (bromomethylene)bis(phosphonate)

Product 1

HCID 88104290diisopropyl 1-bromo-2-[2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorophenyl]vinylphosphonateYield 21.5%

Procedure

Following the procedure described in Example 40 and using 3.4 g (8 mmol) of tetraisopropyl bromomethanediphosphonate, 0.2 g (8 mmol) of sodium hydride and 1.6 g (4 mmol) of 2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorobenzaldehyde, a crude product is obtained whose silica gel chromatography first revealed 0.5 g of diisopropyl 1-bromo-2-[2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorophenyl]vinylphosphonate followed by 0.4 g of diisopropyl 2-[2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorophenyl]ethynylphosphonate.

Sources & evidence

ORD record
ord-77096ed632b14aaea4706601e5a38cc7
Source dataset
uspto-grants-2001_01
Patent number
US06175007B1

Reaction notes

Loading…