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

HRID 901562Notes

Reaction equation

HRID 901562 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

864 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-6f9ed7cac6384ef0a5f7b7d24b033757
Source dataset
uspto-grants-2008_04
Patent number
US07361764B2

Reaction notes

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