Tetrabutylammonium Fluoride → 4-Chloro-1H-indol-5-ol

HRID 450294Notes

Reaction equation

HRID 450294 reaction equation
C([Si](C)(C)[N:6]1[C:14]2[C:9](=[C:10]([Cl:16])[C:11]([OH:15])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:16][C:10]1[C:11]([OH:15])=[CH:12][CH:13]=[C:14]2[C:9]=1[CH:8]=[CH:7][NH:6]2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 674317611-(tert-Butyl-dimethyl-silanyl)-4-chloro-1H-indol-5-ol

Product 1

HCID 445500814-Chloro-1H-indol-5-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-(tert-Butyl-dimethyl-silanyl)-4-chloro-1H-indol-5-ol (5.35 g, 18.98 mmol) is dissolved in THF (90 mL) and cooled to 0° C. TBAF (4.96 g, 18.98 mmol) is added over 5 minutes to the brown solution. After 1 hour the reaction is quenched with ammonium chloride. The reaction is diluted with ethyl acetate and washed with water and then brine. The organic phase is removed, dried (sodium sulfate) and concentrated. The mixture is absorbed onto silica and purified via FCC (0-40% ethyl acetate:heptanes) to obtain the title compound as a solid. MS (ESI) m/z 168.15 (M+1).

Workup

  1. customAfter 1 hour the reaction is quenched with ammonium chloride
  2. additionThe reaction is diluted with ethyl acetate
  3. washwashed with water
  4. customThe organic phase is removed
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated
  7. customThe mixture is absorbed onto silica
  8. custompurified via FCC (0-40% ethyl acetate:heptanes)

Sources & evidence

ORD record
ord-8159a39ff0f24191a21a1a8d63d23ac5
Source dataset
uspto-grants-2013_07
Patent number
US08486954B2

Reaction notes

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