Dimethylformamide → HCID 23300044, compound

HRID 1952761Notes

Reaction equation

HRID 1952761 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH3:9][O:10][CH:11]([O:14][CH3:15])[CH2:12]Br.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:9][O:10][CH:11]([O:14][CH3:15])[CH2:12][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 23300044HCID 23300044, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 2-bromophenol (34.8 ml), bromoacetaldehyde dimethyl acetal (35.5 ml), potassium carbonate (124.4 g) and dimethylformamide (500 ml) was stirred at 95° C. under nitrogen for 18 hours, then cooled and poured onto cold water (500 ml). The product was extracted into ether (2×300 ml) and the combined extracts were washed with saturated aqueous sodium bicarbonate solution (300 ml) and brine (300 ml) and dried (MgSO4). The solvent was removed in vacuo to give 2-(2-bromophenoxy) acetaldehyde dimethyl acetal as an oil (69.6 g).

Workup

  1. temperaturecooled
  2. extractionThe product was extracted into ether (2×300 ml)
  3. washthe combined extracts were washed with saturated aqueous sodium bicarbonate solution (300 ml) and brine (300 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f1da431801fc4610b97397c572c25e74
Source dataset
uspto-grants-2000_09
Patent number
US06114334

Reaction notes

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