Tetrabutylammonium Fluoride → HCID 53709988, compound

HRID 343028Notes

Reaction equation

HRID 343028 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([F:13])[C:3]=1[CH:14]([O:16][Si](C(C)(C)C)(C)C)[CH3:15].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOCC>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([F:13])[C:3]=1[CH:14]([OH:16])[CH3:15]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 53916178HCID 53916178, compound

Product 1

HCID 53709988HCID 53709988, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-chloro-2-fluoro-3-(1-t-butyldimethylsilyloxyethyl)benzoate (25 g) and tetrabutylammonium fluoride (210 ml of 1.0M solution in THF) were dissolved in THF and stirred for 4 hours at room temperature. The mixture was diluted with ether and washed with water. The organic extract was dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness yielding ethyl 4chloro-2-fluoro-3-(1-hydroxyethyl)benzoate (16.8 g) as a clear oil, NMR (CDCl3) 1.3(t,3H), 1.5(d,3H), 2.5(bs,1H), 4.3(q,2H), 5.3(q,1H), 7.1(d,1H), 7.7(t,1H).

Workup

  1. washwashed with water
  2. extractionThe organic extract
  3. dry with materialwas dried (anhydrous magnesium sulphate)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-923166b750c149ed80eff9dc00072b80
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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