Tetrabutylammonium Fluoride → HCID 67246085, compound

HRID 1927527Notes

Reaction equation

HRID 1927527 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21](=[O:47])[C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([Br:29])=[C:24]([S:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[C:33]=2[O:39][Si](C(C)(C)C)(C)C)[CH:23]=1>O1CCCC1>[CH3:19][O:20][C:21](=[O:47])[C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([Br:29])=[C:24]([S:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[C:33]=2[OH:39])[CH:23]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67246220HCID 67246220, compound

Product 1

HCID 67246085HCID 67246085, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tetra-n-butylammonium fluoride (6.12 g, 19 mmol) in tetrahydrofuran (20 mL) was added dropwise to a solution of 4-bromo-3-[2-(tert-butyl-dimethyl-silanyloxy)-3-chloro-benzylsulfanyl]-5-methyl-benzoic acid methyl ester (5 g, 96.9 mmol) in tetrahydrofuran (50 mL) under nitrogen at 5° C. and stirring was continued for 0.5 h. It was concentrated, treated with chilled water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, ethyl acetate/pet ether) to obtain the title compound as a white solid. Yield: 3.0 g, (95%); 1H NMR (CDCl3): δ 2.42 (s, 3H, CH3), 3.88 (s, 3H, OCH3), 4.34 (s, 2H, CH2), 6.81 (t, 1H, Ar), 7.29 (t, 2H, Ar), 7.7 (s, 2H, Ar); MS: m/e (EI+) 401 (M+).

Workup

  1. concentrationIt was concentrated
  2. additiontreated with chilled water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. customdried
  6. concentrationconcentrated
  7. custompurified

Sources & evidence

ORD record
ord-648528a369c84210a7b1159ca456745b
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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