1-Bromo-3-chloropropane → Methyl 5-(3-chloropropoxy)-2-nitrobenzoate

HRID 631337Notes

Reaction equation

HRID 631337 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].Br[CH2:16][CH2:17][CH2:18][Cl:19]>>[Cl:19][CH2:18][CH2:17][CH2:16][O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

3

Reactant 2

HCID 80061-Bromo-3-chloropropaneHCID 12922678Methyl 5-hydroxy-2-nitrobenzoate

Product 1

HCID 66638743Methyl 5-(3-chloropropoxy)-2-nitrobenzoateYield 94%

Procedure

Methyl 5-hydroxy-2-nitrobenzoate (4.37 g, 22.17 mmol, prepared as previously described), and 1-bromo-3-chloropropane (6.58 mL, 66.5 mmol) were reacted using the procedure described in Example 40A Step 3 to give methyl 5-(3-chloropropoxy)-2-nitrobenzoate (5.70 g, 20.8 mmol, 94%). 1H NMR (300 MHz, DMSO-d6) δ 8.14 (d, 1H), 7.33 (d, 1H), 7.30 (dd, 1H), 4.27 (dt, 2H), 3.86 (s, 3H), 3.68 (t, 2H), 2.21 (t, 2H); LC-MS (ESI) m/z 274 (M+H)+.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-8a22ade2e43a411eae91e9119e13fbdf
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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