Pyridine → 2-(Bromomethyl)-2-(2,4-dichlorophenyl)-4-propyloxolane

HRID 462890Notes

Reaction equation

HRID 462890 reaction equation
ClC1C=CC(C2(C[Br:17])CCC(CCC)O2)=CC=1.[OH:18][CH2:19][CH:20]([CH2:32][CH2:33][CH3:34])[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[Cl:31])=[CH2:23].BrBr.N1C=CC=CC=1>ClCCl>[Cl:31][C:25]1[CH:26]=[C:27]([Cl:30])[CH:28]=[CH:29][C:24]=1[C:22]1([CH2:23][Br:17])[CH2:21][CH:20]([CH2:32][CH2:33][CH3:34])[CH2:19][O:18]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24408BromineHCID 13235820HCID 13235820, compoundHCID 20281497HCID 20281497, compound

Product 1

HCID 202814842-(Bromomethyl)-2-(2,4-dichlorophenyl)-4-propyloxolaneYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By the cyclisation procedure described for the preparation of 2-(4-chlorophenyl)-2-bromomethyl-5-prop-1-yltetrahydrofuran (see Example 1), 4-(hydroxymethyl)-2-(2,4-dichlorophenyl)hept-1-ene (1.5 g), bromine (0.88 g), and pyridine (0.43 g) in dry dichloromethane (30 ml) gave 2-(2,4-dichlorophenyl)-2-bromomethyl-4-prop-1-yltetrahydrofuran (1.9 g, 98%) as a pale yellow oil.

Sources & evidence

ORD record
ord-f7cd8993e23b4f23ab5a55761a8a2ddc
Source dataset
uspto-grants-1985_05
Patent number
US04518415

Reaction notes

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