Morpholine → 4-(2-Bromo-3-methylbenzoyl)morpholine

HRID 1028944

Reaction equation

HRID 1028944 reaction equation
[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>C1COCC1>[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[O:6]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 27355882-Bromo-3-methylbenzoic acid

Product 1

HCID 712534814-(2-Bromo-3-methylbenzoyl)morpholine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-bromo-3-methylbenzoic acid (2.19 g, 10.18 mmol) in THF (20.37 mL) was treated with N,N′-carbonyldiimidazole (1.98 g, 12.2 mmol). The reaction mixture was stirred at ambient temperature overnight (14 h). Morpholine (3.11 mL, 35.6 mmol) was added in one portion. The resulting solution was stirred for 8 h and then partitioned between EtOAc and water. Organic layer washed with water, dilute HCl, saturated aqueous Na2CO3, water and brine. The solution was then concentrated in vacuo to afford (2-bromo-3-methylphenyl)(morpholino)methanone as a white crystalline solid.

Workup

  1. stirringThe resulting solution was stirred for 8 h
  2. custompartitioned between EtOAc and water
  3. washOrganic layer washed with water, dilute HCl, saturated aqueous Na2CO3, water and brine
  4. concentrationThe solution was then concentrated in vacuo

Sources & evidence

ORD record
ord-c902d1751206421ea8ee7456a09c5f15
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Linked notes

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