N-bromobutanimide → 2-Bromo-4-(4-propylmorpholin-2-yl)phenol

HRID 600230Notes

Reaction equation

HRID 600230 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][O:7][CH:6]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH2:5]1)[CH2:2][CH3:3].[Br:17]N1C(=O)CCC1=O>ClCCl>[Br:17][C:12]1[CH:11]=[C:10]([CH:6]2[O:7][CH2:8][CH2:9][N:4]([CH2:1][CH2:2][CH3:3])[CH2:5]2)[CH:15]=[CH:14][C:13]=1[OH:16]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 444439424-(4-Propylmorpholin-2-yl)phenol

Product 1

HCID 574406772-Bromo-4-(4-propylmorpholin-2-yl)phenolYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the phenol from example 29 (200 mg 0.9 mmol) in dichloromethane (5 ml) was added N-bromosuccinimide (161 mg, 0.9 mmol). The reaction mixture was stirred at room temperature for 55 hours, before concentrating in vacuo. The crude product was purified by column chromatography on silica eluting with dichloromethane, methanol (95:5) to give the title compound as a white foam (117.5 mg, 0.35 mmol, 44%). 1H NMR (CDCl3, 400 MHz) δ: 0.96 (t, 3H), 1.59 (q, 2H), 2.03 (t, 1H), 2.23 (t, 1H), 2.40 (t, 2H), 2.81 (d, 1H), 2.98 (d, 1H), 3.82 (t, 1H), 4.01 (d, 1H), 4.56 (d, 1H), 6.96 (d, 1H), 7.20 (d, 1H), 7.49 (s, 1H). LRMS: m/z 302 (M-H+, Br isotope).

Workup

  1. concentrationbefore concentrating in vacuo
  2. customThe crude product was purified by column chromatography on silica eluting with dichloromethane, methanol (95:5)

Sources & evidence

ORD record
ord-c07103fb1ae64e7c96768dbf40af33b1
Source dataset
uspto-grants-2011_03
Patent number
US07902188B2

Reaction notes

Loading…