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Ethanol → Ethyl 2-fluoro-3-methylbenzoate

HRID 2171647
Notes
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Reaction equation

HRID 2171647 reaction equation
[F:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:17][CH2:18]O>>[F:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:17][CH3:18])=[O:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 27373792-Fluoro-3-methylbenzoic acid

Product 1

HCID 46311374Ethyl 2-fluoro-3-methylbenzoate

Conditions

Temperature
90 °C

Procedure

2-Fluoro-3-methylbenzoic acid (8.0 g) was mixed with EtOH (100 ml), and concentrated sulfuric acid was added thereto, followed by stirring at 90° C. overnight. The reaction mixture was concentrated under reduced pressure, and EtOAc and water were then added thereto. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, then dried over Na2SO4, and concentrated under reduced pressure to obtain ethyl 2-fluoro-3-methylbenzoate (7.84 g).

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and EtOAc and water
  3. additionwere then added
  4. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f6db904f0020462c833aaf92140e88fb
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09051283B2

Reaction notes

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