Tetrabutylammonium Fluoride → 3-Bromo-6-chloro-2-(3-hydroxypropyl)-5-(4-methoxybenzyl)phenol

HRID 2206776Notes

Reaction equation

HRID 2206776 reaction equation
[Br:1][C:2]1[C:7]([CH2:8][CH2:9][CH2:10][OH:11])=[C:6]([O:12][Si](C(C)(C)C)(C)C)[C:5]([Cl:20])=[C:4]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Br:1][C:2]1[C:7]([CH2:8][CH2:9][CH2:10][OH:11])=[C:6]([OH:12])[C:5]([Cl:20])=[C:4]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 867140833-(6-Bromo-2-((tert-butyldimethylsilyl)oxy)-3-chloro-4-(4-methoxybenzyl)phenyl)propan-1-ol

Product 1

HCID 867140843-Bromo-6-chloro-2-(3-hydroxypropyl)-5-(4-methoxybenzyl)phenolYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of alcohol 187 (1.73 g, 3.46 mmol) in THF (28 mL) was added TBAF (1 M in THF, 7.0 mL, 6.92 mmol) at 0° C. The mixture was stirred for 1 hr at rt. The mixture was extracted with EtOAc/aq. sat'd NH4Cl solution (500 mL/50 mL). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the product 188 (1.19 g, 89%).

Workup

  1. extractionThe mixture was extracted with EtOAc/aq
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f2c0ad07e95c4872ab2c34a888ae0dc7
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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