Tetrabutylammonium Fluoride → HCID 53709988, compound

HRID 1288773Notes

Reaction equation

HRID 1288773 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 4-chloro-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-33c879e122a94f2c927c76e6cb44549b
Source dataset
uspto-grants-1998_05
Patent number
US05747424

Reaction notes

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