Boron tribromide → HCID 45119101, compound

HRID 2175834Notes

Reaction equation

HRID 2175834 reaction equation
[F:1][C:2]1[C:9]([O:10]C)=[CH:8][CH:7]=[C:6]([F:12])[C:3]=1[C:4]#[N:5].B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[C:6]([F:12])[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 37918322,6-Difluoro-3-methoxybenzonitrile

Product 1

HCID 45119101HCID 45119101, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,6-difluoro-3-methoxybenzonitrile (4.42 g, 26.1 mmol) was dissolved in DCM (10 mL) at 0° C. then 1 M BBr3 (52.2 mL, 52.2 mmol) was added. The reaction mixture was then warmed up to RT and stirred overnight. The reaction mixture was poured into ice water and extracted with more DCM. The organic layer was separated, dried over Na2SO4, filtered, and evaporated to dryness to yield 2,6-difluoro-3-hydroxybenzonitrile: LC-MS: M+1=156.

Workup

  1. extractionextracted with more DCM
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-fab6aff7e66b46719a4b896678eb9053
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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