N-bromobutanimide → HCID 66967418, compound

HRID 926238Notes

Reaction equation

HRID 926238 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[O:10][CH3:11].ClC1C=CC(C)=C(OC)C=1.C1C(=O)[N:26](Br)[C:24](=O)C1>C(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:9][C:5]1[C:4]([O:10][CH3:11])=[C:3]([CH2:2][CH2:24][NH2:26])[CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 2928585-CHLORO-2-METHYLANISOLEHCID 19390097HCID 19390097, compound

Product 1

HCID 66967418HCID 66967418, compound

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 6212ChloroformSolvent

Procedure

1-(bromomethyl)-3-chloro-2-methoxybenzene. A mixture of 4-chloro-2-methoxy-1-methylbenzene (26.5 g, 169 mmol), NBS (33.1 g, 186 mmol) and benzoyl peroxide (200 mg, 0.826 mmol) in CHCl3 was heated to reflux for 24 h. The reaction was allowed to cool to RT and then concentrated in vacuo. The residue was stirred with petroleum ether and the resulting suspension was filtered off and the filtrate was concentrated in vacuo to give the title compound (30.9 g) as brown oil, which was used as it is in the next step. UPLC (2 min) rt 1.708 min.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 h
  3. concentrationconcentrated in vacuo
  4. filtrationthe resulting suspension was filtered off
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5704c7ec77fe40f696e68774708bafdc
Source dataset
uspto-grants-2016_03
Patent number
US09284331B2

Reaction notes

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