4-Iodophenol → HCID 17607451, compound

HRID 2066618Notes

Reaction equation

[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH:11]1[CH2:13][O:12]1>>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH:11]2[CH2:13][O:12]2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 108944-Iodophenol

HCID 18430Epibromohydrin

Product 1

HCID 17607451HCID 17607451, compoundYield 89%

Procedure

Alkylation of 4-iodophenol with 2-(bromomethyl)oxirane (76) as in Example 2A for 52 h, followed by chromatography of the product on silica gel, eluting with 0-10% CH2Cl2/petroleum ether (foreruns) and then with 20-25% CH2Cl2/petroleum ether, gave 2-[(4-iodophenoxy)methyl]oxirane (79) (reported by Apparu et al., 2000 using glycidyl tosylate) (89%) as a white solid: mp (CH2Cl2/petroleum ether) 67-68° C.; 1H NMR (CDCl3) δ 7.56 (dt, J=9.0, 2.7 Hz, 2H), 6.70 (dt, J=9.0, 2.7 Hz, 2H), 4.20 (dd, J=11.1, 3.1 Hz, 1H), 3.92 (dd, J=11.1, 5.7 Hz, 1H), 3.33 (m, 1H), 2.90 (dd, J=4.8, 4.3 Hz, 1H), 2.74 (dd, J=4.9, 2.6 Hz, 1H).

Workup

washeluting with 0-10% CH2Cl2/petroleum ether (foreruns)

Sources & evidence

ORD record: ord-52bb7895e1e8458bad750ff072f551a2
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293734B2

Reaction notes

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