Water → 3,4-Bis(2-morpholinoethoxy)bromobenzene

HRID 1820102Notes

Reaction equation

HRID 1820102 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([OH:11])[C:7](=[CH:9][CH:10]=1)[OH:8].Cl.Cl[CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.[OH2:22]>CN(C=O)C>[O:19]1[CH2:20][CH2:21][N:16]([CH2:15][CH2:14][O:11][C:6]2[CH:5]=[C:4]([Br:3])[CH:10]=[CH:9][C:7]=2[O:8][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:22][CH2:18][CH2:17]2)[CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 284874-BromocatecholHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 670611913,4-Bis(2-morpholinoethoxy)bromobenzeneYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

64 mg (36.0 mmol) of sodium hydride was added to a suspension of 900 mg (5.0 mmol) of 4-bromocatechol and 3.72 g (20.0 mmol) of 2-chloroethylmorpholine hydrochloride in 50 ml of anhydrous DMF at 0° C. over 25 minutes. The mixture was stirred for 3 days at room temperature. 5 ml water was added to quench the reaction. After removal of the solvent, the black oily residue was adsorbed onto celite and the resulting solid washed with ethyl acetate. The filtrate was then concentrated to give 0.75 g (1.81 mmol; 36% yield) of 3,4-bis(2-morpholinoethoxy)bromobenzene as a hygroscopic yellow solid. 1H-NMR (CD3OD) δ: 8.42 [1H] d (2.0 Hz), 8.18 [1H] d (1.5 Hz), 7.64 [1H] s, 7.56 [1H] dd (1.5 Hz, 7.5 Hz), 7.30 [1H] dt (1.5 Hz, 7.5 Hz), 7.25 [1H] d (2.5 Hz), 7.19 [1H] dd (2.5 Hz, 8.5 Hz), 7.12 [1H] d (8.5 Hz), 7.08 [1H] d (8.5 Hz), 7.05 [1H] dt (1 Hz, 7.5 Hz) 4.25 [2H] t (5.75 Hz), 4.20 [2H] t (5.5 Hz), 3.72 [8H] m, 2.84 [4H] m, 2.66 [8H] m. MS: 559.2 [MH+].

Workup

  1. customto quench
  2. customthe reaction
  3. customAfter removal of the solvent
  4. washthe resulting solid washed with ethyl acetate
  5. concentrationThe filtrate was then concentrated

Sources & evidence

ORD record
ord-631d2209f27844099a4866c0ebe922bf
Source dataset
uspto-grants-2009_10
Patent number
US07601839B2

Reaction notes

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