Benzyl Bromide → HCID 21913792, compound

HRID 1007999Notes

Reaction equation

HRID 1007999 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[OH-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[CH2:14]([O:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 10236NinhydrinHCID 14798Sodium HydroxideHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 21913792HCID 21913792, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a mechanically stirred mixture of tert-butyl 2-(hydroxy)ethylcarbamate (32.2 g, 200.4 mmol) and sodium hydroxide (300 mL of 50%) was added benzyltrimethylammonium chloride (3.79 g, 20.4 mmol) and benzyl bromide (23.8 mL, 200.4 mmol). After stirring at room temperature for 12 hours TLC monitoring, using 1/1 hexane/ethyl acetate and ninhydrin stain, indicated complete reaction. The resulting clear solution was diluted with ice water (1 L), and the organic layer was separated. The aqueous layer was washed with chloroform (4×). The organic layers were combined and washed with water (2×) and brine (2×), dried with sodium sulfate, and concentrated under reduced pressure to provide 45.4 g of clear liquid. NMR analysis confirmed the product, which was used in the next step.

Workup

  1. customreaction
  2. customthe organic layer was separated
  3. washThe aqueous layer was washed with chloroform (4×)
  4. washwashed with water (2×) and brine (2×)
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0b2a339dabfa4f518464ec8456ff3b6a
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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