Diethyl Ether → (5-Bromo-2-fluorobenzyl)-carbamic acid ethyl ester

HRID 606826Notes

Reaction equation

HRID 606826 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].Cl.[Br:8][C:9]1[CH:10]=[CH:11][C:12]([F:17])=[C:13]([CH:16]=1)[CH2:14][NH2:15].C(N(C(C)C)CC)(C)C.C(OCC)C>ClCCl>[CH2:5]([O:4][C:2](=[O:3])[NH:15][CH2:14][C:13]1[CH:16]=[C:9]([Br:8])[CH:10]=[CH:11][C:12]=1[F:17])[CH3:6]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 27249035-Bromo-2-fluorobenzylamine hydrochloride

Product 1

HCID 60755056(5-Bromo-2-fluorobenzyl)-carbamic acid ethyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add ethyl chloroformate (0.24 mL, 2.49 mmol) to a solution of 5-bromo-2-fluorobenzylamine hydrochloride (500 mg, 2.08 mmol) in dichloromethane (8 mL) and diisopropylethylamine (0.90 mL, 5.20 mmol). After 3 h dilute the reaction with diethyl ether and wash twice with 1 N hydrochloric acid and once with an aqueous saturated solution of sodium chloride. Dry (sodium sulfate), filter, and concentrate to give the title compound as a colorless oil (0.527 g, 92%).

Workup

  1. additionAfter 3 h dilute
  2. washwash twice with 1 N hydrochloric acid and once with an aqueous saturated solution of sodium chloride
  3. dry with materialDry (sodium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-e8353b7f59fb426daf148b5ba28ff67a
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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