Boron tribromide → HCID 59829751, compound

HRID 2223325Notes

Reaction equation

HRID 2223325 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:19]C)=[C:6]([CH2:8][CH2:9][C:10]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:11]=2[C:12]#[N:13])[CH:7]=1.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:19])=[C:6]([CH2:8][CH2:9][C:10]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:11]=2[C:12]#[N:13])[CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22744933HCID 22744933, compound

Product 1

HCID 59829751HCID 59829751, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 2-[2-(5-bromo-2-methoxyphenyl)-ethyl]-3-chlorobenzonitrile (0.187 g, 1.0 equiv) in CH2Cl2 (2.5 mL) was allowed to stir under an atmosphere of argon at −78° C. To this solution was added boron tribromide (1.0 M in CH2Cl2, 2.65 mL, 5.0 equiv). After 15 min at −78° C., the solution was allowed to warm to room temperature and stir overnight. The reaction was quenched by the addition of water and the solution was extracted with EtOAc. The organic phase was dried over Na2SO4, filtered and concentrated. The residue was purified by column chromotagraphy (SiO2, 20% EtOAc in hexane) to give 2-[2-(5-bromo-2-hydroxyphenyl)-ethyl]-3-chlorobenzonitrile (0.144 g, 81%).

Workup

  1. temperatureto warm to room temperature
  2. stirringstir overnight
  3. customThe reaction was quenched by the addition of water
  4. extractionthe solution was extracted with EtOAc
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromotagraphy (SiO2, 20% EtOAc in hexane)

Sources & evidence

ORD record
ord-b08aaa0274f54632bb51220a2cbc67ea
Source dataset
uspto-grants-2008_05
Patent number
US07375125B2

Reaction notes

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