Methanol → Methyl 2-(2-acetyl-5-bromophenoxy)acetate

HRID 1479744Notes

Reaction equation

HRID 1479744 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([OH:11])[CH:3]=1.[H-].[Na+].Br[CH2:15][C:16]([O:18][CH3:19])=[O:17].CO>CN(C)C=O>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[O:11][CH2:15][C:16]([O:18][CH3:19])=[O:17])(=[O:10])[CH3:9]

Participants

6

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 107274031-(4-Bromo-2-hydroxyphenyl)ethan-1-one

Product 1

HCID 57419482Methyl 2-(2-acetyl-5-bromophenoxy)acetateYield 96.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(4-bromo-2-hydroxyphenyl)ethanone (1.06 g, 5 mmol) in dry N,N-dimethylformamide (10 mL) was charged with sodium hydride (240 mg, 10 mmol) and the mixture was stirred at room temperature for 30 minutes, then methyl 2-bromoacetate (0.84 g, 5.5 mmol) was added and the mixture was stirred at room temperature for 12 hours. After completed (40 mL) of methanol was added followed by concentrating under vacuum to give methyl 2-(2-acetyl-5-bromophenoxy)acetate (1.38 g, 90%) as colorless oil. 1H NMR (300 MHz, CD3OD) δ 8.01 (s, 1H), 7.65 (d, J=8.1 Hz, 1H), 7.18 (d, J=8.1 Hz, 1H), 6.97 (s, 1H), 4.73 (s, 2H), 3.81 (s, 3H), 2.69 (s, 3H).

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. additionwas added
  3. concentrationby concentrating under vacuum

Sources & evidence

ORD record
ord-2625d9aa14e24e4e8352ba8e3177310c
Source dataset
uspto-grants-2016_08
Patent number
US09409865B2

Reaction notes

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