Water → HCID 4508433, compound

HRID 898539Notes

Reaction equation

HRID 898539 reaction equation
CCN(C(C)C)C(C)C.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([Cl:18])[CH:12]=1.Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].O>CN(C=O)C>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:13]([Cl:18])[CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 198594-Bromo-2-chlorophenolHCID 81531Diisopropylethylamine

Product 1

HCID 4508433HCID 4508433, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

14.5 mL (83.242 mmol) Hünig base was added to a solution of 7.800 g (37.222 mmol) 4-bromo-2-chlorophenol and 4.70 mL (41.537 mmol) ethyl bromoacetate in 100 mL DMF and the mixture was stirred for 4 h at 100° C. The reaction mixture was combined with water and exhaustively extracted with EtOAc. The combined org. phases were washed with saturated aqueous sodium bicarbonate, water and saturated aqueous NaCl, dried over sodium sulphate and evaporated down i. vac. The crude product was used in the next reaction step without any further purification.

Workup

  1. extractionexhaustively extracted with EtOAc
  2. washphases were washed with saturated aqueous sodium bicarbonate, water and saturated aqueous NaCl
  3. dry with materialdried over sodium sulphate
  4. customevaporated down i
  5. customThe crude product was used in the next reaction step without any further purification

Sources & evidence

ORD record
ord-db4923892c22486e904a16a501c48049
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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