Sodium Hydroxide → HCID 71006766, compound

HRID 1477234Notes

Reaction equation

HRID 1477234 reaction equation
[Br:1][C:2]#[C:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[CH:6][CH:5]=1.[OH-].[Na+]>CO.C1COCC1.O>[Br:1][C:2]#[C:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10966594methyl 4-(bromoethynyl)benzoate

Product 1

HCID 71006766HCID 71006766, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of methyl 4-(bromoethynyl)benzoate (67 g, 280 mmol) in CH3OH/THF/H2O=5/5/1 (1100 mL) was added NaOH (44.84 g) and the reaction mixture was stirred at 25° C. for 3 hr. The volatiles were removed under reduced pressure and the resulting solution was neutralized with 1 N HCl to pH 3-5. Solids were collected by filtration, washed with water and dried at 50° C. for 5 hr to yield 4-(bromoethynyl)benzoic acid (INT-1) (61 g, 96%).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. filtrationSolids were collected by filtration
  3. washwashed with water
  4. customdried at 50° C. for 5 hr

Sources & evidence

ORD record
ord-71fbb31b82a440599c07f0b2c4ac7fa4
Source dataset
uspto-grants-2016_08
Patent number
US09403758B2

Reaction notes

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