Cesium fluoride → 1-(5-Bromothiophen-2-yl)-2,2,2-trifluoroethanol

HRID 1715347Notes

Reaction equation

HRID 1715347 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[F-].[Cs+].[Si]([C:15]([F:18])([F:17])[F:16])(C)(C)C>C(COC)OC>[Br:1][C:2]1[S:6][C:5]([CH:7]([OH:8])[C:15]([F:18])([F:17])[F:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 784285-Bromothiophene-2-carbaldehydeHCID 552549(Trifluoromethyl)trimethylsilane

Product 1

HCID 199715801-(5-Bromothiophen-2-yl)-2,2,2-trifluoroethanol

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of 5-bromothiophene-2-carboxaldehyde (1.0 equiv) in dry glyme at RT, was added CsF (0.1 eq.) followed by dropwise addition of TMSCF3 (1.2 eq.). The reaction mixture was stirred for 2 hr, then quenched by adding 3N HCl and stirred for 30 min. The organics were extracted with DCM and the organic extracts were combined and washed with brine and dried (Na2SO4). Evaporation of the solvent gave the crude product which was purified by flash column chromatography on silica using 1-10% EtOAc/Petroleum ether to yield the desired compound as an oil. 1H NMR (300 MHz, CDCl3, 300K) δ 7.00 (1H, d, J=3.7 Hz), 6.94 (1H, d, J=3.7 Hz), 5.18 (1H, q, J=6.2 Hz), 3.61 (1H, broad s).

Workup

  1. customquenched
  2. additionby adding 3N HCl
  3. stirringstirred for 30 min
  4. extractionThe organics were extracted with DCM
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent
  8. customgave the crude product which
  9. customwas purified by flash column chromatography on silica using 1-10% EtOAc/Petroleum ether

Sources & evidence

ORD record
ord-41c29f29f59c47a79c3ac3ba8d5eb791
Source dataset
uspto-grants-2010_09
Patent number
US07799825B2

Reaction notes

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