4-Hydroxybenzaldehyde → HCID 11492677, compound

HRID 714441Notes

Reaction equation

HRID 714441 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+]>CN(C=O)C.O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:3][CH:4]=1)=[O:7]

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

Product 1

HCID 11492677HCID 11492677, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

2.54 g (20.81 mmol) of 4-hydroxybenzaldehyde were initially charged in 50 ml of DMF. 5.13 g (22.89 mmol) of tert-butyl (2-bromoethyl)carbamate, 10.17 g (31.25 mmol) of cesium carbonate and 0.78 g (5.20 mmol) of sodium iodide were added, and the mixture was then stirred at 65° C. overnight. Water was added, and the reaction mixture was extracted three times with ethyl acetate. The combined organic phases were washed in each case twice with 1N aqueous sodium hydroxide solution, saturated aqueous ammonium chloride solution and water, dried over sodium sulfate, filtered and concentrated.

Workup

  1. extractionthe reaction mixture was extracted three times with ethyl acetate
  2. washThe combined organic phases were washed in each case twice with 1N aqueous sodium hydroxide solution, saturated aqueous ammonium chloride solution and water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-877b59583afb4468a0d84f9b098fdf65
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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