Tetrabutylammonium Fluoride → HCID 68455108, compound

HRID 2357548Notes

Reaction equation

HRID 2357548 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][Si](C(C)(C)C)(C)C)=[C:4]([F:17])[C:3]=1[I:18].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][OH:7])=[C:4]([F:17])[C:3]=1[I:18]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68452317HCID 68452317, compound

Product 1

HCID 68455108HCID 68455108, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (4-chloro-2-fluoro-3-iodobenzyloxy)(tert-butyl)dimethylsilane (6.64 g, 16.6 mmol) in THF (60 mL) was added tetrabutylammonium fluoride, 1.0 M in THF (19.9 mL, 19.9 mmol). The reaction solution was stirred at RT for 1 h. The volatile solvents were removed in vacuo. The residue was diluted with diethyl ether (150 mL), and then washed with saturated aqueous solution of sodium bicarbonate, and brine. The resulting organic solution was then dried over magnesium sulfate and concentrated under reduced pressure. Flash chromatography on silica gel (dichloromethane) gave (4-chloro-2-fluoro-3-iodophenyl)methanol as a colorless oil. 1H NMR (300 MHz, CDCl3) δ ppm 7.16-7.32 (2H, m), 4.66 (2H, d, J=5.7 Hz), 1.90 (1H, t, J=6.0 Hz)

Workup

  1. customThe volatile solvents were removed in vacuo
  2. additionThe residue was diluted with diethyl ether (150 mL)
  3. washwashed with saturated aqueous solution of sodium bicarbonate, and brine
  4. dry with materialThe resulting organic solution was then dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9080f37f31514a48a253c41ffdf421c5
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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