Potassium Carbonate → HCID 59829157, compound

HRID 2061408Notes

Reaction equation

HRID 2061408 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:11])[C:9]=1[OH:10])[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:11])[C:9]=1[O:10][CH2:24][C:23]1[CH:26]=[CH:27][C:20]([O:19][CH3:18])=[CH:21][CH:22]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 181003,5-Dibromo-4-HydroxybenzaldehydeHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 59829157HCID 59829157, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 3,5-dibromo-4-hydroxybenzaldehyde (5.30 g, 18.9 mmol) in anhydrous DMF (15 mL) under nitrogen was added potassium carbonate (5.50 g, 19.9 mmol) and the mixture was stirred for 10-15 min during which time vigorous effervescence was observed. 4-methoxybenzyl chloride (2.70 mL, 19.9 mL) was then added and the mixture was heated at 60° C. for 20 h. The mixture was filtered and the filtrate was evaporated. The residual oil was then poured into water (100 mL) and the mixture was stirred for 1-2 h. The resulting solid was collected by filtration, washed with water and dried under vacuum at 60° C. to leave 6.63 g (88%) of the title compound as a pale brown solid. 1H NMR (DMSO-d6) 3.82 (3 H, s), 5.06 (2 H, s), 7.02 (2 H, d), 7.53 (2 H, d), 8.24 (2 H, s), 9.95 (1 H, s).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. additionThe residual oil was then poured into water (100 mL)
  4. stirringthe mixture was stirred for 1-2 h
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with water
  7. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-f631ea8d2ea142409d89e9577e1ef48e
Source dataset
uspto-grants-2012_10
Patent number
US08283351B2

Reaction notes

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