2-Bromotoluene → 4-o-tolylmorpholine

HRID 412755Notes

Reaction equation

HRID 412755 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.CC(C)([O-])C.[Na+]>>[CH3:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Participants

4

Reactant 3

HCID 72362-BromotolueneHCID 8083MorpholineHCID 23676156Sodium t-butoxide

Product 1

HCID 98153874-o-tolylmorpholineYield 40%

Procedure

According to the general procedure B, 2-bromotoluene (171 mg, 1.00 mmol) reacted with morpholine (104 mg, 1.20 mmol) using 1 mol % of catalyst and sodium tert-butoxide (134 mg, 1.40 mmol) at room temperature for 43 h to give the title compound (70 mg, 40%) as an oil after purification: 1H-NMR (300 MHz, CDCl3): δ 7.22-7.18 (m, 2H), 7.06-7.00 (m, 2H), 3.87 (t, 4H, J=4.5 Hz), 2.93 (t, 4H, J=4.5 Hz), 2.34 (s, 3H). GC/MS(EI): m/z 177 (M+).

Workup

  1. customat room temperature
  2. customfor 43 h

Sources & evidence

ORD record
ord-8b08dbdb623c4d9ebc05f76e3c684ef8
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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