Triethylamine → HCID 9860085, compound

HRID 2400234Notes

Reaction equation

HRID 2400234 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Br)=[O:4].[C:7]([O:12][CH2:13][CH2:14][OH:15])(=[O:11])[C:8]([CH3:10])=[CH2:9].C(N(CC)CC)C.COC1C=CC(O)=CC=1>C(OCC)(=O)C>[C:7]([O:12][CH2:13][CH2:14][O:15][C:3](=[O:4])[CH:2]([Br:1])[CH3:6])(=[O:11])[C:8]([CH3:10])=[CH2:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 90154-MethoxyphenolHCID 133602-Hydroxyethyl MethacrylateHCID 79047Propanoyl bromide, 2-bromo-

Product 1

HCID 9860085HCID 9860085, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

2-Bromopropionyl bromide (18 g, 0.083 mol, 1 m.e) in ethyl acetate (30 mL) was added dropwise to a mixture of 2-hydroxyethyl methacrylate (HEMA) (16.26 g, 0.125 mol, 1.5 m.e) and triethylamine (9.26 g, 0.091 mol, 1.1 m.e) in ethyl acetate (80 mL) at 0° C. under a N2 environment. Hydroquinone monomethyl ether (MEHQ) was added as an inhibitor at this stage (−15 mg, 1.2×10−4 mol). The reaction mixture was stirred overnight, then filtered, further treated with more MEHQ (˜15 mg) and then evaporated to dryness to give a clear colourless oil (14 g, 0.053 mol, 63% yield). 1H NMR (200 MHz, CDCl3) δ 1.82 (d, J=8 Hz, 3H, CH3CH—), 1.95 (s, 3H, (CH3CCO—), 4.36-4.46 (m, 5H, 2× —CH2O— and —CHBr), 5.60 (br. s, 1H, vinyl), 6.13 (s, 1H, vinyl) ppm.

Workup

  1. filtrationfiltered
  2. additionfurther treated with more MEHQ (˜15 mg)
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-3e0a866ac84246e2a9186cf5236c4666
Source dataset
uspto-grants-2014_08
Patent number
US08795782B2

Reaction notes

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