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

HRID 1279036Notes

Reaction equation

HRID 1279036 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-fa6f8721b9b84d1f86933518507ba1a1
Source dataset
uspto-grants-2002_09
Patent number
US06444672B1

Reaction notes

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