Diethyl Ether → HCID 68510931, compound

HRID 1715862Notes

Reaction equation

HRID 1715862 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].CCOCC.[Br:16]Br>C(O)(=O)C>[BrH:16].[Br:16][C:8]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[C:4]([CH:7]=1)[CH2:5][NH2:6]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24408BromineHCID 812922-Methoxybenzylamine

Product 1

HCID 68510931HCID 68510931, compoundYield 141.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 2-methoxybenzylamine (30 mmol, 4.12 g) was added ether (6 ml) and acetic acid (glacial, 10 ml). The resulting solution was cooled on an ice-batch and Br2 (30 mmol, 4.79 g, 1.54 ml) was added dropwise. After 1 h the ice-bath was removed and the mixture was stirred for another 1 h before addition of ether (20 ml). The resulting mixture was left in the cold for 0.5 h, the solids were filtered off and washed with ether (20 ml) to give a cream colored solid (6.29 g). The crude product was crystallized in ethanol/ether to give the title compound (4.62 g, 52%) as white crystalline material. 1H NMR (DMSO, 500 MHz) δ 3.84 (s, 3H), 3.98 (s, 2H), 7.05 (s, 1H), 7.58 (m, 2H) and 8.16. (br, 3H).

Workup

  1. additionwas added dropwise
  2. customAfter 1 h the ice-bath was removed
  3. waitThe resulting mixture was left in the cold for 0.5 h
  4. filtrationthe solids were filtered off
  5. washwashed with ether (20 ml)

Sources & evidence

ORD record
ord-2341f35a69f44e9bb5019267158154e5
Source dataset
uspto-grants-2010_09
Patent number
US07799947B2

Reaction notes

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