Bis(2-bromoethyl) ether → 4-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine

HRID 57529

Reaction equation

HRID 57529 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[C:11]([NH2:15])[CH:12]=[CH:13][CH:14]=2)[O:3]1.Br[CH2:18][CH2:19][O:20][CH2:21][CH2:22]Br.CCN(C(C)C)C(C)C>C1COCC1>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:16])([CH3:1])[O:3][B:4]([C:9]2[CH:10]=[C:11]([N:15]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH:12]=[CH:13][CH:14]=2)[O:5]1

Participants

5

Reactant 3

HCID 21521Bis(2-bromoethyl) etherHCID 81531DiisopropylethylamineHCID 27346553-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 41926634-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine (164 mg, 0.75 mmol), 1-bromo-2-(2-bromoethoxy)ethane (418 mg, 1.8 mmol), and DIPEA (0.64 mL, 3.6 mmol) in THF (2 mL) was stirred at reflux overnight. The mixture was concentrated, diluted with water, and extracted with EtOAc. The combined extracts were dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative thin-layer chromatography to give the title compound. MS (m/z): 290 (M+H)+.

Workup

  1. temperatureat reflux overnight
  2. concentrationThe mixture was concentrated
  3. additiondiluted with water
  4. extractionextracted with EtOAc
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-cc1fb27aad36408cadc3dd063474605a
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Linked notes

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