Tetrabutylammonium Fluoride → HCID 66816832, compound

HRID 1029035Notes

Reaction equation

HRID 1029035 reaction equation
[Br:1][C:2]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:3]=1[NH:4][CH2:5][CH2:6][O:7][Si](C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Br:1][C:2]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:3]=1[NH:4][CH2:5][CH2:6][OH:7]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67376843HCID 67376843, compound

Product 1

HCID 66816832HCID 66816832, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 50-mL RBF was added 2-bromo-N-(2-(tert-butyldimethylsilyloxy)ethyl)-3-methylaniline (1.43 g, 4.15 mmol) and THF (10 mL). A solution of TBAF (1.0M in THF; 4.98 mL, 4.98 mmol) was added dropwise at RT. The reaction mixture was allowed to stir for 1.5 h at RT. The solvent was removed under reduced pressure. The remaining residue was purified by flash chromatography (5-60% EtOAc/hexanes). 2-(2-Bromo-3-methylphenylamino)ethanol was isolated as a clear yellow oil.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe remaining residue was purified by flash chromatography (5-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-14ed5bb12de74f9ea6b8a5ea2ca8c0be
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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