4-Bromophenol → 2-[2-(4-Bromophenoxy)ethoxy]tetrahydro-2H-pyran

HRID 892862Notes

Reaction equation

HRID 892862 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:16][CH2:17][O:18][CH:19]1[CH:24]=[CH:23][CH:22]=[CH:21][O:20]1>CS(C)=O.[Cl-].[Na+].O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:16][CH2:17][O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 78084-BromophenolHCID 184563812-(2-Bromoethoxy)-2H-pyranHCID 23665647Potassium tert-butoxide

Product 1

HCID 128104732-[2-(4-Bromophenoxy)ethoxy]tetrahydro-2H-pyranYield 85%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 4-bromophenol (1.71 g, 9.91 mmol) in DMSO (40 mL) was added potassium t-butoxide (1.17 g, 10.4 mmol) and the mixture was stirred for 20 mins. Tetrahydro-2-(2-bromoethoxy-2H-pyran (2.18 g, 10.4 mmol) in DMSO (10 mL) was added dropwise and the reaction was stirred for 1 hr. It was then diluted with brine (100 mL) and extracted with ethylacetate (3×100 mL). The organics were combined, dried with MgSO4 and concentrated. The resulting residue was chromatographed (silica gel, hexanes:ether, 85:15) to afford tetrahydro-2-(2-(4-bromophenoxy)ethoxy)-2H-pyran (2.52 g, 85%) as a colorless oil.

Workup

  1. stirringthe reaction was stirred for 1 hr
  2. extractionextracted with ethylacetate (3×100 mL)
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated
  5. customThe resulting residue was chromatographed (silica gel, hexanes:ether, 85:15)

Sources & evidence

ORD record
ord-475a0fc9bd754864b424e7c2714274ce
Source dataset
uspto-grants-1992_06
Patent number
US05120752

Reaction notes

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