Tetrabutylammonium Fluoride → 10-Fluoro-4-thia-decanoic acid

HRID 279429Notes

Reaction equation

HRID 279429 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8][CH2:9][CH2:10][C:11]([O:13]C)=[O:12].CCCC[N+](CCCC)(CCCC)CCCC.[F-].[F:33]CCCCCCCCCCCCSCCC(O)=O>[OH-].[K+].C(O)C>[F:33][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 2262515116-Fluoro-4-thia-hexadecanoic acidHCID 22625154Methyl 10-bromo-4-thia-decanoate

Product 1

HCID 2262514810-Fluoro-4-thia-decanoic acidYield 37%

Reagents, catalysts & solvents 1

HCID 21946426Potassium hydroxide ethanolSolvent

Procedure

Compound 5 (0.5 g, 1,8 mmol) was caused to react with TBAF (3 mmol) according to the procedure for compound 2. The resultant fluoroester was hydrolyzed in KOH/ethanol as previously described, and isolated as an oil by HPLC (Table 1) to yield 0.14 g (37% yield) product 6. 1H-NMR δ1.3 (m, 8H, CH2), 2.55 (t, 2H, C(2)H2), 2,65 (t,2H, C(5)H2), 2.80 (t, 2H, C(3)H2), 4.44 (dt, 2H, C(16)H2JHF=47.5 Hz, JHH=6.2 Hz).

Workup

  1. customisolated as an oil by HPLC (Table 1)

Sources & evidence

ORD record
ord-dd69be9d332c45ea973ab975620686b0
Source dataset
uspto-grants-2002_03
Patent number
US06362352B1

Reaction notes

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