Allyl bromide → HCID 22168678, compound

HRID 1977349Notes

Reaction equation

HRID 1977349 reaction equation
CO[C:3](=O)[C:4]1C=C(C=C(N)[CH:15]=1)C(OCC=C)=O.[CH3:18][O:19][C:20](=[O:33])[C:21]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[CH:27]=[C:23]([C:24]([O-:26])=[O:25])[CH:22]=1.C(Br)C=C.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:18][O:19][C:20](=[O:33])[C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([N+:30]([O-:32])=[O:31])[CH:29]=1)[C:24]([O:26][CH2:15][CH:4]=[CH2:3])=[O:25]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 6931682Monomethyl-5-nitroisophthalateHCID 221685801-Methyl 3-(2-propen-1-yl) 5-amino-1,3-benzenedicarboxylate

Product 1

HCID 22168678HCID 22168678, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Starting material (3(b)) was synthesised as follows. A mixture of mono-methyl-5-nitroisophthalate (13.8 g), allyl bromide (7.96 g), potassium carbonate (13.94 g) and DMF (160 ml) was stirred at ambient temperature for 4.5 h. The solid was filtered and DMF was evaporated away from the filtrate under reduced pressure. The residue was dissolved in diethyl ether (300 ml) and water (100 ml) and stirred for five minutes. The organic layer was separated and washed with saturated sodium bicarbonate solution (220 ml), brine (200 ml), dried over magnesium sulphate and evaporated under reduced pressure to give 5-nitro-isophthalic acid allyl ester methyl ester (3(a)) as a yellow oil (14.74 g).

Workup

  1. customwas synthesised
  2. filtrationThe solid was filtered
  3. customDMF was evaporated away from the filtrate under reduced pressure
  4. dissolutionThe residue was dissolved in diethyl ether (300 ml)
  5. stirringwater (100 ml) and stirred for five minutes
  6. customThe organic layer was separated
  7. washwashed with saturated sodium bicarbonate solution (220 ml), brine (200 ml)
  8. dry with materialdried over magnesium sulphate
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4bc15af671fc4e71bdc3fa40bd35db5e
Source dataset
uspto-grants-2001_05
Patent number
US06232338B1

Reaction notes

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