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Ethyl 3-methyl-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate → {2-Methyl-5-[4-(trifluoromethyl)phenyl]thien-3-yl}methanol

HRID 9642
Notes
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Reaction equation

HRID 9642 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[S:4][C:3]=1[C:17](OCC)=O.Br([O-])(=O)=[O:23].[Na+].S(=O)(O)[O-].[Na+]>C1CCCCC1.O>[CH3:17][C:3]1[S:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)=[CH:6][C:2]=1[CH2:1][OH:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 15946279Ethyl 3-methyl-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate2×HCID 23665763Sodium BisulfiteHCID 23668195Sodium Bromate

Product 1

HCID 21986536{2-Methyl-5-[4-(trifluoromethyl)phenyl]thien-3-yl}methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×
HCID 8078
Cyclohexane
Solvent

Procedure

Ethyl 3-methyl-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate (intermediate 35, 0.100 g) and sodium bromate (0.144 g) were suspended in a mixture of cyclohexane and water (1:1 v/v, 4 ml). To this was added a solution sodium bisulfite (0.99 g) in water (1 ml). The mixture was stirred for 2 hours, quenched with 1M sodium thiosulfate solution, then extracted with ethyl acetate. The organic layer was taken and washed with water, sodium thiosulfate and dried with brine and over MgSO4 and concentrated to give the title compound as a white crystalline solid.

Workup

  1. customquenched with 1M sodium thiosulfate solution
  2. extractionextracted with ethyl acetate
  3. washwashed with water, sodium thiosulfate
  4. dry with materialdried with brine and over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-01fd9acbd4244adfb8428d8144a29522
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091237B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes