Hydrochloric Acid → HCID 18786128, compound

HRID 1107878Notes

Reaction equation

HRID 1107878 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:19][C:20]([Si](C)(C)C)([F:22])[F:21].[CH:27]([C:29]1[O:30][C:31]2[C:38]([Br:39])=[CH:37][CH:36]=[CH:35][C:32]=2[C:33]=1[CH3:34])=[O:28].Cl>C1COCC1.O>[F:19][C:20]([F:22])([F:21])[CH:27]([C:29]1[O:30][C:31]2[C:38]([Br:39])=[CH:37][CH:36]=[CH:35][C:32]=2[C:33]=1[CH3:34])[OH:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 18786118HCID 18786118, compound

Product 1

HCID 18786128HCID 18786128, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

14 mg of tetrabutylammonium fluoride and 1.22 ml of trifluoromethyltrimethylsilane, dropwise, are added to a solution, cooled to 0° C. with an ice bath, of 1.58 g (6.6 mmol) of 2-formyl-3-methyl-7-bromobenzofuran in 60 ml of THF. The solution is left stirring for 30 min at 0° C. and then for 1 h at room temperature and a solution of 6 ml of THF and of 3 ml of hydrochloric acid (3M) is added. Stirring is continued for 2 h at room temperature, 100 ml of water are added and extraction is carried out with ethyl acetate (3×60 ml). The organic phases are combined, dried over magnesium sulphate and concentrated. 198 g (Yield: 97%) of 2-(2,2,2-trifluoro-1-hydroxyethyl)-3-methyl-7-bromobenzofuran are obtained--M.p.: 93° C.

Workup

  1. waitThe solution is left
  2. waitfor 1 h at room temperature
  3. stirringStirring
  4. waitis continued for 2 h at room temperature
  5. extractionextraction
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bc213866fd5f46c89480de6659522947
Source dataset
uspto-grants-2000_05
Patent number
US06063810

Reaction notes

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