Phosphorus tribromide → 3-(6-Bromo-3-bromomethyl-2-fluoro-phenoxy)-5-chloro-benzonitrile

HRID 559057Notes

Reaction equation

HRID 559057 reaction equation
P(Br)(Br)[Br:2].[Br:5][C:6]1[C:11]([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[C:19]([Cl:21])[CH:20]=2)[C:16]#[N:17])=[C:10]([F:22])[C:9]([CH2:23]O)=[CH:8][CH:7]=1>C(Cl)Cl>[Br:5][C:6]1[C:11]([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[C:19]([Cl:21])[CH:20]=2)[C:16]#[N:17])=[C:10]([F:22])[C:9]([CH2:23][Br:2])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 669992083-(6-Bromo-2-fluoro-3-hydroxymethyl-phenoxy)-5-chloro-benzonitrile

Product 1

HCID 669997373-(6-Bromo-3-bromomethyl-2-fluoro-phenoxy)-5-chloro-benzonitrileYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of PBr3 (0.74 mL of a 1 M solution in DCM, 1.1 equiv) was added to a solution of 107 (0.24 g, 0.67 mmol) in DCM (5 mL). The mixture was stirred at RT for 1 h and then concentrated in vacuo. The residue was dissolved in EtOAc, washed with saturated aqueous NaHCO3, and dried (MgSO4). Evaporation of the volatile materials afforded 0.17 g (60%) of 96.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the volatile materials

Sources & evidence

ORD record
ord-bcc8d59da0a64c44993373471a9d8321
Source dataset
uspto-grants-2011_11
Patent number
US08063064B2

Reaction notes

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