Hydrochloric Acid → 1227935-03-6

HRID 1020343Notes

Reaction equation

HRID 1020343 reaction equation
O[Li].O.[Br:4][C:5]1[O:6][C:7]([C:14]([O:16]CC)=[O:15])=[C:8]([C:10]([F:13])([F:12])[F:11])[N:9]=1.Cl>C1COCC1.O.CCOC(C)=O.O>[Br:4][C:5]1[O:6][C:7]([C:14]([OH:16])=[O:15])=[C:8]([C:10]([F:12])([F:11])[F:13])[N:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 53403202Ethyl 2-bromo-4-(trifluoromethyl)-1,3-oxazole-5-carboxylate

Product 1

HCID 574617891227935-03-6Yield 88.3%

Reagents, catalysts & solvents 2

HCID 21881883Oxolane--water (1/1)SolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
0 °C

Procedure

LiOH.H2O (0.64 g, 15.25 mmol) was added to a solution of ethyl 2-bromo-4-trifluoromethyloxazole-5-carboxylate (A-2) (3.50 g, 12.2 mmol) in THF/H2O (20/5 mL) at 0° C. followed by stirring for 3 h at 0° C. The reaction mixture was diluted with EtOAc/H2O (25/25 mL) and neutralized with 1 M HCl (16 mL) at 0° C. The organic phase was separated, dried over MgSO4, filtered, and concentrated. The product was dried in vacuo to yield 2-bromo-4-trifluoromethyloxazole-5-carboxylic acid (A-38) as a white solid (2.80 g, 88% yield).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was dried in vacuo

Sources & evidence

ORD record
ord-19fd433f5dfc4a29a3f71291672a81eb
Source dataset
uspto-grants-2014_05
Patent number
US08716312B2

Reaction notes

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