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

HRID 2170484Notes

Reaction equation

HRID 2170484 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-0db8d288376f4d5fa2f9028cbe143cb0
Source dataset
uspto-grants-2015_06
Patent number
US09051269B2

Reaction notes

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