Lithium iodide → 3-Bromo-5-hydroxybenzonitrile

HRID 602591Notes

Reaction equation

HRID 602591 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10]C)[CH:9]=1)[C:5]#[N:6].[Li+].[I-]>N1C(C)=CC(C)=CC=1C>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[C:5]#[N:6]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 250673623-Bromo-5-methoxybenzonitrile

Product 1

HCID 184400433-Bromo-5-hydroxybenzonitrileYield 89.7%

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Conditions

Temperature
150 °C

Procedure

step 3—Anhydrous collidine (100 mL) was added to a dry flask containing 3-bromo-5-methoxy-benzonitrile (10.4 g, 49 mmol) and LiI (19.6 g, 3 equiv). The solution was heated under nitrogen to 150° C. overnight, cooled to RT, and poured into an ice cold 1 M HCl solution. The mixture was extracted with a 1:1 EtOAc/hexanes solution, washed with water, and dried (MgSO4). Concentration in vacuo afforded 8.7 g (89%) of 3-bromo-5-hydroxy-benzonitrile.

Workup

  1. temperaturecooled to RT
  2. extractionThe mixture was extracted with a 1:1 EtOAc/hexanes solution
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-5b284ee2494845ad886b0ca3a2c7306e
Source dataset
uspto-grants-2011_03
Patent number
US07906540B2

Reaction notes

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