Dimethylformamide → HCID 22609149, compound

HRID 2306541Notes

Reaction equation

HRID 2306541 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[C:18]([OH:19])=[C:17]([Br:20])[CH:16]=[CH:15][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11].CN(C)C=O.Br[CH2:27][CH:28]1[CH2:31][CH2:30][CH2:29]1>O>[Br:7][C:8]1[C:18]([O:19][CH2:27][CH:28]2[CH2:31][CH2:30][CH2:29]2)=[C:17]([Br:20])[CH:16]=[CH:15][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2734658(Bromomethyl)cyclobutaneHCID 14851207Ethyl 2,4-dibromo-3-hydroxybenzoate

Product 1

HCID 22609149HCID 22609149, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

2.990 g (21.60 mmol) of potassium carbonate and 3.050 g (9.40 mmol) of ethyl 2,4-dibromo-3-hydroxybenzoate were introduced into 50 ml of N,N-dimethylformamide. 1.401 g (9.40 mmol) of bromomethylcyclobutane were added at room temperature and the mixture was heated for 6 hours at 120-130° C. The mixture was subsequently poured into water and extracted with diethyl ether. The combined organic phases were washed with water, dried over Na2SO4 and evaporated completely on a rotary evaporator. Drying in an oil-pump vacuum gave ethyl 2,4-dibromo-3-cyclobutylmethoxybenzoate as brown oil.

Workup

  1. extractionextracted with diethyl ether
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated completely on a rotary evaporator
  5. customDrying in an oil-pump vacuum

Sources & evidence

ORD record
ord-60f0b5aaa1944cd2b555cb3d13daddcb
Source dataset
uspto-grants-2004_12
Patent number
US06828276B2

Reaction notes

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