Ammonia → ({3-[(3-Bromo-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)amine

HRID 1875147Notes

Reaction equation

HRID 1875147 reaction equation
[NH3:1].[Br:2][C:3]1[CH:4]=[C:5]([O:10][C:11]2[C:16]([F:17])=[C:15]([CH2:18]Br)[CH:14]=[CH:13][C:12]=2[Cl:20])[CH:6]=[C:7]([Cl:9])[CH:8]=1>C(Cl)Cl>[Br:2][C:3]1[CH:4]=[C:5]([O:10][C:11]2[C:16]([F:17])=[C:15]([CH2:18][NH2:1])[CH:14]=[CH:13][C:12]=2[Cl:20])[CH:6]=[C:7]([Cl:9])[CH:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 684836772-[(3-Bromo-5-chlorophenyl)oxy]-4-(bromomethyl)-1-chloro-3-fluorobenzene

Product 1

HCID 68487182({3-[(3-Bromo-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)amineYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask containing ammonia (7.0 M solution in methanol) (132 ml, 927 mmol) was added a solution of 2-[(3-bromo-5-chlorophenyl)oxy]-4-(bromomethyl)-1-chloro-3-fluorobenzene (4.97 g, 11.59 mmol) in DCM (15 ml) dropwise and the mixture was stirred overnight at room temperature. The solvent was removed and the crude material was purified via silica gel chromatography to give ({3-[(3-bromo-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)amine (3.70 g, 10.14 mmol, 87% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.34-7.85 (m, 3H), 7.06 (s, 1H), 6.99 (t, 1H), 3.72 (s, 2H), 1.85 (s, 2H).

Workup

  1. customThe solvent was removed
  2. customthe crude material was purified via silica gel chromatography

Sources & evidence

ORD record
ord-e58c92c1af8b416c9443c4cfa6664a86
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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