Hydrochloric Acid → HCID 64854928, compound

HRID 1754965Notes

Reaction equation

HRID 1754965 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:19])[CH2:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:9]=1.Cl>CO.C1COCC1>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([NH:7][CH2:6][C:5]([OH:19])=[O:4])=[CH:9][C:10]=1[C:15]([F:16])([F:17])[F:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 40044612HCID 40044612, compound

Product 1

HCID 64854928HCID 64854928, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A 2 N aqueous NaOH solution (15.0 ml, 30.0 mmol) was added to a solution of (4-bromo-3-trifluoromethyl-phenylamino)-acetic acid methyl ester (4.30 g, 13.8 mmol) in methanol-THF (6:1, 35.0 ml), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was made acidic with hydrochloric acid and extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, and then dried over MgSO4 and concentrated under reduced pressure to give (4-bromo-3-trifluoromethyl-phenylamino)-acetic acid (4.03 g, 98%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was sequentially washed with water and saturated brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9aa01ad08cda41d49a57450f6f606ece
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

Loading…