Phosphorus tribromide → HCID 68981267, compound

HRID 349447Notes

Reaction equation

HRID 349447 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[N:12]=[N:11][C:10]([C:13]3[CH:14]=[C:15]([CH2:19]O)[CH:16]=[CH:17][CH:18]=3)=[N:9]2)=[CH:5][CH:4]=1.P(Br)(Br)[Br:24]>ClCCl>[Br:24][CH2:19][C:15]1[CH:14]=[C:13]([C:10]2[N:11]=[N:12][N:8]([CH2:7][C:6]3[CH:21]=[CH:22][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:9]=2)[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 68981248HCID 68981248, compound

Product 1

HCID 68981267HCID 68981267, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The alcohol (1 g, 3.37 mmol) of Step (a) was dissolved in dichloromethane (25 mL) and added dropwise at room temperature to a solution of phosphorous tribromide (1 g, 3.7 mmol) in dichloromethane (75 mL). The solution was stirred for 16 hours, then concentrated in vacuo. The residue obtained was triturated with hexane and collected by filtration to yield a white solid (1.17 g, 92%). 1H NMR (CDCl3) δ 8.2 (d, 1H), 7.7 (m, 2H), 7.5 (m, 1H), 7.4 (d, 2H), 6.8 (d, 2H), 5.8 (s, 2H), 4.5 (s, 2H), 3.7 (s, 3H) ppm.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue obtained
  3. customwas triturated with hexane
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-6a317fcc2c8f42e38fcbbeb0054c81eb
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Reaction notes

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