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

HRID 1874938Notes

Reaction equation

HRID 1874938 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[C:15]([F:16])=[C:14]([CH2:17]Br)[CH:13]=[CH:12][C:11]=2[Cl:19])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH3:20]>C(Cl)Cl.CO>[Br:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[C:15]([F:16])=[C:14]([CH2:17][NH2:20])[CH:13]=[CH:12][C:11]=2[Cl:19])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

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 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[(3-bromo-5-chlorophenyl)oxy]-4-(bromomethyl)-1-chloro-3-fluorobenzene (2.0 g, 4.7 mmol) in CH2Cl2 (10 mL) was added ammonia in methanol (7N, 100 mL). The reaction mixture was stirred for 4 h and concentrated. The resulting crude material was triturated from water to afford the title compound (1.55 g, 92%) as a white solid. 1H NMR (400 MHz, DMSO-d5): δ ppm 7.57-7.49 (m, 3H), 7.12-7.11 (m, 1H), 7.05-7.04 (m, 1H), 5.99 (br s, 2H), 3.95 (s, 2H).

Workup

  1. concentrationconcentrated
  2. customThe resulting crude material was triturated from water

Sources & evidence

ORD record
ord-ce3c09e53cc54c7bb6b1e985878503d4
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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