4-Nitrobenzyl bromide → HCID 18977580, compound

HRID 1489204Notes

Reaction equation

HRID 1489204 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][C:6](=[O:8])[CH:5]=[CH:4][CH2:3]1.[N+:10]([C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1)([O-:12])=[O:11].C(C1C(O[SiH](C)C)=C(Br)C(OC)=CC=1CC1C(=O)C=CCC1(C)C)(C)(C)C>>[N+:10]([C:13]1[CH:20]=[CH:19][C:16]([CH2:17][CH:7]2[C:6](=[O:8])[CH:5]=[CH:4][CH2:3][C:2]2([CH3:9])[CH3:1])=[CH:15][CH:14]=1)([O-:12])=[O:11]

Participants

4

Reactant 3

HCID 660114-Nitrobenzyl bromideHCID 1383222-Cyclohexenone, 5,5-dimethyl-HCID 178488804HCID 178488804, compound

Product 1

HCID 18977580HCID 18977580, compound

Procedure

This compound was prepared from 5,5-dimethylcyclohex-2-en-1-one (11) (0.600 g, 4.83 mmol) and p-nitrobenzyl bromide (1.581 g, 7.32 mmol) in the manner previously described for the synthesis of enone 13, affording 627 mg (50%), of the nitro-enone as a pale yellow oil. 1H NMR (400MHz, CDCl3) δ1.02 and 1.18 (2s, 2×3H, geminal-CH3 's), 2.83 and 3.10 (d of ABq, 2H, benzylic-CH2), 6.00 (ddd, 1H, 2-H), 6.81 (ddd, 1H, 3-H), 7.38 and 8.10 ppm (ABq, 2×2H, Ar--H).

Workup

  1. customaffording 627 mg (50%)

Sources & evidence

ORD record
ord-4314a9ec410949dc87e26f22f7affd10
Source dataset
uspto-grants-1997_10
Patent number
US05677336

Reaction notes

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