2,2,2-Trifluoroethanol → HCID 86668529, compound

HRID 1405412Notes

Reaction equation

HRID 1405412 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[Na+].[Cl:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=1[CH:20](Br)Br)[C:13]([O:15]C)=[O:14].[OH-:23].[Na+]>CN(C=O)C.O>[F:1][C:2]([F:6])([F:5])[CH2:3][O:4][CH:20]([O:23][CH2:3][C:2]([F:6])([F:5])[F:1])[C:19]1[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[Cl:9]

Participants

7

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 68731754HCID 68731754, compound

Product 1

HCID 86668529HCID 86668529, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,2,2-trifluoroethanol (109 μL, 1.50 mmol) in DMF (2.63 mL) was added NaH (64 mg, 1.6 mmol). The mixture was stirred at room temperature for 1 h before methyl 3-chloro-4-(dibromomethyl)benzoate (342 mg, 1.00 mol) was added. The mixture was stirred at room temperature for 2 h before it was poured into water and was extracted with EtOAc (3×). The organics were combined, washed with water, brine, dried (Na2SO4) and evaporated to dryness. The material was taken up in MeOH and powdered NaOH (160 mg, 4.00 mol) was added and the mixture was stirred at room temperature for 1 h. The mixture was evaporated and treated with 1N HCl (until the solution was strongly acidic). The precipitated product was washed with water and dried to give 4-(bis(2,2,2-trifluoroethoxy)methyl)-3-chlorobenzoic acid. ESI-MS m/z calc. 394.4, found 394.5 (M+1)+; Retention time: 1.74 minutes (3 min run).

Workup

  1. additionwas added
  2. extractionwas extracted with EtOAc (3×)
  3. washwashed with water, brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness
  6. stirringthe mixture was stirred at room temperature for 1 h
  7. customThe mixture was evaporated
  8. additiontreated with 1N HCl (until the solution
  9. washThe precipitated product was washed with water
  10. customdried

Sources & evidence

ORD record
ord-1cebd54e8407415686865c9f3da6ebbe
Source dataset
uspto-grants-2014_12
Patent number
US08916565B2

Reaction notes

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