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

HRID 2102350Notes

Reaction equation

HRID 2102350 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, 0.39 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-70d76c6fd8b645d6b696112738e9c027
Source dataset
uspto-grants-2009_08
Patent number
US07576081B2

Reaction notes

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