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Hydrochloric Acid → 2-Bromo-4-(trifluoromethoxy)benzoic acid

HRID 1873837
Notes
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Reaction equation

HRID 1873837 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[C:13]1[O:14]CC(C)(C)N=1.Cl.[OH2:21]>>[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:10])([F:11])[F:12])[CH:5]=[CH:4][C:3]=1[C:13]([OH:14])=[O:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 594473872-[2-Bromo-4-(trifluoromethoxy)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole

Product 1

HCID 594474442-Bromo-4-(trifluoromethoxy)benzoic acid

Conditions

Temperature
90 °C

Procedure

To a 50 ml round bottom flask fitted with a magnetic stirring bar and a reflux condensor was loaded 2-[2-bromo-4-(trifluoromethoxy)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole (0.56 g, 1.66 mmol) and 10 ml 5N HCl. The reaction mixture was heated at 90° C. overnight. After cooling to room temperature, the reaction mixture was diluted with 20 ml water and extracted with 40 ml ethyl acetate. The extracts were dried over sodium sulfate, filtered and concentrated to give 0.42 g light brown solid.

Workup

  1. customTo a 50 ml round bottom flask fitted with a magnetic stirring bar
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with 40 ml ethyl acetate
  4. dry with materialThe extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e44e4764e92f46d3b2290dfef7cfae9b
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08304434B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes