Water → HCID 67439902, compound

HRID 1664304Notes

Reaction equation

HRID 1664304 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][Si](C(C)(C)C)(C)C)=[CH:4][C:3]=1[CH2:16][O:17][CH2:18][O:19][CH3:20].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH2:16][O:17][CH2:18][O:19][CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 66738564HCID 66738564, compound

Product 1

HCID 67439902HCID 67439902, compoundYield 110.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-bromo-4-tert-butyldimethylsiloxy-2-methoxymethoxymethylbenzene (34.2 g, 94.8 mmol) in tetrahydrofuran (100 mL) was added tetrabutylammonium fluoride (1 mol/L in tetrahydrofuran, 50 mL), and the mixture was stirred at room temperature for 1 hour. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (2:1 hexane/ethyl acetate) to give 4-bromo-3-(methoxymethoxymethyl)phenol (25.9 g, quant).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (2:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6bf9c30d1fca4c41a149023367ed7ec4
Source dataset
uspto-grants-2011_10
Patent number
US08039450B2

Reaction notes

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