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

HRID 1971410Notes

Reaction equation

HRID 1971410 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-9cee1dfd93e040408b9fa0b1f5ed617f
Source dataset
uspto-grants-2013_04
Patent number
US08431584B2

Reaction notes

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