3,4-dihydro-2H-pyran → 2-Bromo-5-fluoro-1-(tetrahydropyran-2-yloxy)benzene

Reaction equation

[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[Br:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=1[OH:32]>>[Br:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=1[O:32][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1

Participants

Reactant 3

HCID 80803,4-dihydro-2H-pyran

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

HCID 27246002-Bromo-5-fluorophenol

Product 1

HCID 593402342-Bromo-5-fluoro-1-(tetrahydropyran-2-yloxy)benzene

Procedure

Procedure analogous to Example 5. Use of 478.0 ml (5.24 mol) of 3,4-dihydropyran, 65.4 g (260 mmol) of pyridinium p-toluenesulfonate and 500.0 g (2.62 mmol) of 2-bromo-5-fluorophenol. The yield was 562.2 g (78.0%) at a purity of greater than 98.0% by 1H NMR.

Sources & evidence

ORD record: ord-29fd321e5b3e42b0917b52b8342edecd
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728137B2

Reaction notes

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