Dichloromethane → 4-Butoxy-2-methyl-1-nitrobenzene

HRID 2174512Notes

Reaction equation

HRID 2174512 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].Br[CH2:16]CCC.C(Cl)Cl>O>[CH2:9]([O:8][C:6]1[CH:5]=[CH:4][C:3]([N+:12]([O-:14])=[O:13])=[C:2]([CH3:1])[CH:7]=1)[CH2:10][CH2:11][CH3:16]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8002Butyl bromideHCID 231345792-Methyl-1-nitro-4-propoxybenzene

Product 1

HCID 692098674-Butoxy-2-methyl-1-nitrobenzeneYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

This compound was prepared in a similar manner to that for 404b except 1-bromobutane was deployed for the alkyl ether adduct and the partition step during workup utilized DCM (150 mL) and water (150 mL) to provide a yellow oil (2.0 g, 99%): TLC Rf 0.70 (20% EtOAc/hexanes). 1H NMR (600 MHz, CDCl3) δ 8.09-8.07 (d, 1H, J=8.88 Hz), 6.79-6.76 (m, 2H), 4.03-4.01 (t, 2H, J=6.48 Hz), 2.63 (s, 3H), 1.80-1.78 (quin, 2H, J=7.44 Hz), 1.53-1.47 (sex, 2H, J=7.44 Hz), 1.0-0.97 (t, 3H, J=7.38 Hz). 13C NMR (150 MHz, CDCl3) δ 162.7, 141.9, 137.1, 127.6, 117.9, 112.2, 68.3, 31.0, 21.8, 19.1, 13.8. Elemental analysis calculated for C11H15NO3: C, 63.14; H, 7.23; N, 6.69. Found: C, 63.25; H, 7.09; N, 6.69.

Sources & evidence

ORD record
ord-439d11b3829c4ab6b877b0c6710588e1
Source dataset
uspto-grants-2015_06
Patent number
US09061994B1

Reaction notes

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