Diethylamine → HCID 57559812, compound

HRID 1724067Notes

Reaction equation

HRID 1724067 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([B:9]2[O:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH2:11][O:10]2)[CH:6]=[CH:7][CH:8]=1.[CH2:17]([NH:19][CH2:20][CH3:21])[CH3:18]>C(OCC)(=O)C>[CH3:15][C:12]1([CH3:16])[CH2:13][O:14][B:9]([C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[CH2:2][N:19]([CH2:20][CH3:21])[CH2:17][CH3:18])[O:10][CH2:11]1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 38449612-[3-(bromomethyl)phenyl]-5,5-dimethyl-1,3,2-dioxaborinane

Product 1

HCID 57559812HCID 57559812, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

2-(3-Bromomethyl-phenyl)-5,5-dimethyl-[1,3,2]dioxaborinane (0.21 mmol, 60 mg) and diethyl-amine (1 mL, >10 equiv) were combined and left to stir at 70° C. for 4 hours. The reaction mixture was then diluted with ethyl acetate, concentrated in vacuo and dried on high vacuum for 1 hour. The residue was then dissolved in dichloromethane, washed with water, followed by brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the final product as yellow oil (37.7 mg, 65%). 1H NMR (300 MHz, CDCl3): δ (ppm)=7.71 (m, 2H), 7.44 (m, 1H), 7.33 (m, 1H), 3.79 (s, 4H), 3.59 (s, 2H), 2.54 (q, 4H), 1.06 (t, 6H), 1.04 (s, 6H).

Workup

  1. waitleft
  2. concentrationconcentrated in vacuo
  3. customdried on high vacuum for 1 hour
  4. dissolutionThe residue was then dissolved in dichloromethane
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d103af6d85284a29b8b87786820e2aca
Source dataset
uspto-grants-2009_02
Patent number
US07485722B2

Reaction notes

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