4-Bromophenol → 4-(4-Bromophenoxy)tetrahydro-2H-pyran

HRID 1008511Notes

Reaction equation

HRID 1008511 reaction equation
C(OC(N=NC(OCC)=O)=O)C.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.O[CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 78084-BromophenolHCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 162161274-(4-Bromophenoxy)tetrahydro-2H-pyran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 4.0 mL of diethyl-azodicarboxylate in 20 mL of dry tetrahydrofuran was added at 5° C. to a stirred solution of 3.5 g of 4-bromo-phenol, 2.4 mL of 4-hydroxy-tetrahydropyran and 6.6 g triphenylphosphine in 75 mL of tetrahydrofuran within 30 minutes. Stirring was continued at room temperature for 72 hours. The solvent was evaporated in vacuo and the residue chromatographed on silica gel (ethyl acetate) yielding 5.6 g of 4-(4-bromo-phenoxy)-tetrahydropyran as a white solid. M.p 53-55° C., EI-MS: 256 (M+).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue chromatographed on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-fa37aa3017474b488d549c3ea9c09380
Source dataset
uspto-grants-2004_09
Patent number
US06797710B2

Reaction notes

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