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

HRID 1874914Notes

Reaction equation

HRID 1874914 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([O:12][C:13]2[CH:18]=[C:17]([Br:19])[CH:16]=[C:15]([F:20])[C:14]=2[Cl:21])[C:6]=1[F:22])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[Br:19][C:17]1[CH:16]=[C:15]([F:20])[C:14]([Cl:21])=[C:13]([O:12][C:7]2[C:6]([F:22])=[C:5]([CH2:4][NH2:1])[CH:10]=[CH:9][C:8]=2[Cl:11])[CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 866448931-(Azidomethyl)-3-[(5-bromo-2-chloro-3-fluorophenyl)oxy]-4-chloro-2-fluorobenzene

Product 1

HCID 68480394({3-[(5-Bromo-2-chloro-3-fluorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)amineYield 73.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(azidomethyl)-3-[(5-bromo-2-chloro-3-fluorophenyl)oxy]-4-chloro-2-fluorobenzene (8.3 g, 20.29 mmol) dissolved in THF (100 mL) was treated successively with triphenylphosphine (7.98 g, 30.4 mmol) and water (1.828 g, 101 mmol) at 25° C. for 2 days with stirring. The reaction mixture was concentrated to dryness and purified on 330 g silica gel eluted successively with EtOAc (to remove triphenylphosphine oxide) followed by 0 to 10% CH3OH/DCM to give ({3-[(5-bromo-2-chloro-3-fluorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)amine (5.73 g, 14.96 mmol, 73.7% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.48-7.63 (m, 3H), 6.71 (s, 1H), 3.77 (s, 2H), 1.90 (s, 2H). LC-MS (ES−) m/z 380.00, 381.97, 384.06 [M−1]. LC-MS (ES+) m/z 381.84, 383.83, 385.87 [M+H].

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. custompurified on 330 g silica gel
  3. washeluted successively with EtOAc (to remove triphenylphosphine oxide)

Sources & evidence

ORD record
ord-40c382bbd30f4a77bed7bd45cfdd3d1a
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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