Pyridine → 2-(Bromomethyl)-2-(4-chlorophenyl)-5,5-dimethyloxolane

HRID 462883Notes

Reaction equation

HRID 462883 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:16][Br:17])[CH2:12][CH2:11][CH:10]([CH2:13]CC)[O:9]2)=[CH:4][CH:3]=1.Cl[C:19]1C=CC(C(CCC(O)(C)C)=C)=CC=1.BrBr.N1C=CC=CC=1>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:16][Br:17])[CH2:12][CH2:11][C:10]([CH3:13])([CH3:19])[O:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24408BromineHCID 13235820HCID 13235820, compoundHCID 20281502HCID 20281502, compound

Product 1

HCID 202815002-(Bromomethyl)-2-(4-chlorophenyl)-5,5-dimethyloxolane

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), 2-(4-chlorophenyl)-5-hydroxy-5-methylhex-1-ene (5.3 g), bromine (3.8 g), and pyridine (1.9 g), in dichloromethane (60 ml), gave 2-(4-chlorophenyl)-2-bromomethyl-5,5-dimethyltetrahydrofuran (7.6 g) as a red oil, 1H nmr (CDCl3): δ1.2 (3H, singlet) and 1.4 (3H, singlet), 2×CH3, 3.5 (2H, singlet, CH2Br).

Sources & evidence

ORD record
ord-26cfb2b5e00b492998baaa589f77ddc1
Source dataset
uspto-grants-1985_05
Patent number
US04518415

Reaction notes

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