2-Bromophenol → HCID 11087925, compound

HRID 558136Notes

Reaction equation

HRID 558136 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[H-].[Na+].Br[CH2:12][CH2:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1>CN(C=O)C.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:12][CH2:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1

Participants

7

Reactant 3

HCID 72442-BromophenolHCID 24758Sodium hydrideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyran

Product 1

HCID 11087925HCID 11087925, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add 2-bromo-phenol (10 g, 57.80 mmol) to a suspension of sodium hydride (60% dispersion in mineral oil, 2.77 g, 69.36 mmol) in DMF (6 mL). Stir the mixture for 1 h. Add 2-(2-bromo-ethoxy)-tetrahydropyran (13.54 g, 64.74 mmol). Stir the solution at RT overnight. Dilute the mixture with ethyl acetate and water. Wash the organic layer with aqueous saturated sodium chloride and water. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo. Purify by column chromatography (10% ethyl acetate in hexane) to give the title compound (13.9 g, 80%) as a light yellow oil. MS (ES) m/z 323 [M+Na]+.

Workup

  1. stirringStir the solution at RT overnight
  2. washWash the organic layer with aqueous saturated sodium chloride and water
  3. dry with materialDry the mixture over sodium sulfate
  4. concentrationConcentrate the solution in vacuo
  5. customPurify by column chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-e30cde16d02647e6b12e615e0f721108
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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