Allyl bromide → HCID 66770474, compound

HRID 1697728Notes

Reaction equation

HRID 1697728 reaction equation
Cl.[NH2:2][C@H:3]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[C:4]([O:6][CH3:7])=[O:5].Br[CH2:16][CH:17]=[CH2:18]>ClCCl>[CH3:7][O:6][C:4](=[O:5])[C@H:3]([NH:2][CH2:18][CH:17]=[CH2:16])[C:8]1[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 44890856Methyl (2R)-amino(4-chlorophenyl)acetate--hydrogen chloride (1/1)

Product 1

HCID 66770474HCID 66770474, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

In a 25 mL round-bottomed flask, (R)-methyl 2-amino-2-(4-chlorophenyl)acetate hydrochloride (1.000 g, 4.24 mmol, Eq: 1.00) and 3-bromoprop-1-ene (564 mg, 394 μL, 4.66 mmol, Eq: 1.1) were combined with dichloromethane (10.0 mL) to give a light yellow solution. The reaction mixture was heated to 22° C. and stirred for 1 h. The reaction mixture was stirred at 25° C. for 18 h. The crude reaction mixture was concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 40 g, 25% to 60% EtOAc in hexanes) to yield the title compound (331 mg; 33%) as a yellow oil. MS (ESI): m/z=376.1 [M+H]+.

Workup

  1. customto give a light yellow solution
  2. stirringThe reaction mixture was stirred at 25° C. for 18 h
  3. customThe crude reaction mixture
  4. concentrationwas concentrated in vacuo
  5. customThe crude material was purified by flash chromatography (silica gel, 40 g, 25% to 60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-63b12909e6ea4c68ac21b53fb766c46e
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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