Dimethylformamide → HCID 22321992, compound

HRID 496646Notes

Reaction equation

HRID 496646 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5].Br[CH2:13][CH2:14][OH:15].CN(C)C=O>>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:13][CH2:14][OH:15])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 108982-Bromoethanol2×HCID 5283822,6-Dichloro-4-hydroxybenzaldehyde2×

Product 1

HCID 22321992HCID 22321992, compound

Conditions

Temperature
80 °C

Procedure

To a solution of 3.00 g (15.7 mmol) A1 and 1.4 ml (19.7 mmol) 2-bromoethanol in 50 ml dry dimethyl formamide 3.06 g (22.1 mmol) potassium carbonate were added the mixture was heated to 80° C. for 2 hours. Every 30 minutes, 0.2 ml 2-bromoethanol were added until no A1 was longer observed by TLC (hexanes/ethyl acetate 1:1). The solvent was removed in vacuo and the residue was partitionated between ethyl acetate and water. The organic layer was dried over sodium sulfate and evaporated to dryness. The residue was treated with ether and filtered off to yield 3.03 g (82%) A12, m.p. 83-85° C.

Workup

  1. customThe solvent was removed in vacuo
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated to dryness
  4. additionThe residue was treated with ether
  5. filtrationfiltered off
  6. customto yield 3.03 g (82%) A12, m.p. 83-85° C.

Sources & evidence

ORD record
ord-0ac10729745f4c47a6b2984fc2c0ed8a
Source dataset
uspto-grants-2005_09
Patent number
US06946471B2

Reaction notes

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