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Hydrochloric Acid → HCID 59571040, compound

HRID 2192902
Notes
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Reaction equation

HRID 2192902 reaction equation
C([O:3][C:4](=[O:18])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([S:13][CH:14]2[CH2:16][CH2:15]2)=[C:9]([Br:17])[CH:8]=1)=[O:6])C.[OH-].[Na+].O.Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:17][C:9]1[CH:8]=[C:7]([C:5](=[O:6])[C:4]([OH:18])=[O:3])[CH:12]=[CH:11][C:10]=1[S:13][CH:14]1[CH2:15][CH2:16]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 59570898Ethyl [3-bromo-4-(cyclopropylsulfanyl)phenyl](oxo)acetate

Product 1

HCID 59571040HCID 59571040, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 1140
Toluene
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A solution of ethyl[3-bromo-4-(cyclopropylsulfanyl)phenyl](oxo)acetate (30 g) in toluene (60 mL) was heated to 50° C., and a 3 M aqueous sodium hydroxide solution (36 mL) was added thereto at an internal temperature of 60° C. or lower, followed by stirring at 50° C. for 1 hour. After leaving it to be cooled at room temperature, water (150 mL) and ethyl acetate (100 mL) were added to the reaction mixture. To the aqueous layer was added concentrated hydrochloric acid (12 mL) under ice-cooling, followed by extraction with ethyl acetate (100 mL×3). The organic layer was washed with saturated brine (100 mL) and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The residue was sequentially washed with hexane/ethyl acetate (19/1, 200 mL) and diethyl ether/hexane (1/2, 200 mL) to obtain [3-bromo-4-(cyclopropylsulfanyl)phenyl](oxo)acetic acid (14.7 g) as a pale yellow solid.

Workup

  1. customat an internal temperature of 60° C.
  2. customAfter leaving it
  3. temperatureto be cooled at room temperature
  4. temperaturecooling
  5. extractionfollowed by extraction with ethyl acetate (100 mL×3)
  6. washThe organic layer was washed with saturated brine (100 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was then evaporated under reduced pressure
  9. washThe residue was sequentially washed with hexane/ethyl acetate (19/1, 200 mL) and diethyl ether/hexane (1/2, 200 mL)

Sources & evidence

ORD record
ord-29ab79ee9a85418c98246572707858c5
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08329707B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes