Ammonia → HCID 86644921, compound

HRID 1875070Notes

Reaction equation

HRID 1875070 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:16]([F:17])=[C:15]([CH2:18]Br)[CH:14]=[C:13]([Br:20])[C:12]=2[Br:21])[CH:9]=1)[C:5]#[N:6].[NH3:22].CO>ClCCl>[NH2:22][CH2:18][C:15]1[C:16]([F:17])=[C:11]([O:10][C:8]2[CH:7]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:9]=2)[C:5]#[N:6])[C:12]([Br:21])=[C:13]([Br:20])[CH:14]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 86644922HCID 86644922, compound

Product 1

HCID 86644921HCID 86644921, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-chloro-5-{[2,3-dibromo-5-(bromomethyl)-6-fluorophenyl]oxy}benzonitrile (0.185 g, 0.371 mmol) and 7M ammonia in methanol (5 mL, 35.0 mmol) in dichloromethane (5 mL) was stirred at RT overnight. The solvent was evaporated and the residue was purified by chromatography (MeOH:dichloromethane) to give the desired product (37 mg, 19.5%) as a white solid. 1H NMR (400 MHz, methanol-d4) δ ppm 7.80 (d, 1H), 7.52 (t, 1H), 7.25 (t, 1H), 7.20 (d, 1H), 3.82 (s, 2H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by chromatography (MeOH:dichloromethane)

Sources & evidence

ORD record
ord-d109ba5f829f4eab94494229c26e4a7d
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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