Allyl bromide → HCID 13983553, compound

HRID 1084930Notes

Reaction equation

HRID 1084930 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[CH:8]=[CH2:9].[Br:11][C:12]1[CH:13]=[C:14]([OH:22])[C:15](=[CH:20][CH:21]=1)[C:16]([O:18][CH3:19])=[O:17]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.C(#N)C>[CH2:9]([O:22][C:14]1[CH:13]=[C:12]([Br:11])[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])[CH:8]=[CH2:7]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 13983552Methyl 4-bromo-2-hydroxybenzoate

Product 1

HCID 13983553HCID 13983553, compound

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

139 g of ground potassium carbonate, 470 ml of acetonitrile, 16 g of benzyltributylammonium chloride and 136 g of allyl bromide were introduced into a 3-liter round-bottomed flask and 236 g of ground methyl 4-bromosalicylate were added in small amounts. The contents were heated under reflux with vigorous stirring, for 5 hours and then a part of the acetonitrile was distilled off under slight vacuum and the residue was taken up with water. A precipitate of methyl 2-allyloxy-4-bromobenzoate was obtained, which was drained, washed with water and air-dried.

Workup

  1. temperatureThe contents were heated
  2. temperatureunder reflux with vigorous stirring, for 5 hours
  3. distillationa part of the acetonitrile was distilled off under slight vacuum

Sources & evidence

ORD record
ord-8b110b6f6b7f4decb0b671250ea806c4
Source dataset
uspto-grants-1991_04
Patent number
US05006570

Reaction notes

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