聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 3,4-Bis(2-morpholinoethoxy)bromobenzene

HRID 729872

反应方程式

HRID 729872 反应方程式
[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

参与物

6

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 24758氢化钠HCID 284874-溴邻苯二酚HCID 77210N-(2-氯乙基)吗啉盐酸盐

产物 1

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

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

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+].

后处理

  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

来源与证据

ORD记录
ord-fd3f00ecbf9a48c2a4077d262bbcd660
来源数据集
uspto-grants-2009_09
专利号
US07582637B2

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