Bromobenzene → HCID 56982933, compound

HRID 1680226Notes

Reaction equation

HRID 1680226 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]2[CH2:8][C@H:9]3[N:21]([CH3:22])[CH2:20][CH2:19][C@@:15]4([C:16]=2[C:17]=1[OH:18])[C@@:10]3([O:24][CH3:25])[CH2:11][CH2:12][C:13](=[O:23])[CH2:14]4.Br[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>N1C=CC=CC=1>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]2[CH2:8][C@H:9]3[N:21]([CH3:22])[CH2:20][CH2:19][C@@:15]4([C:16]=2[C:17]=1[O:18][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C@@:10]3([O:24][CH3:25])[CH2:11][CH2:12][C:13](=[O:23])[CH2:14]4

Participants

5

Reactant 3

HCID 7961BromobenzeneHCID 11430Potassium CarbonateHCID 86737785HCID 86737785, compound

Product 1

HCID 56982933HCID 56982933, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of crude 16 (16 g) in dry pyridine (200 ml) was added bromobenzene (22.5 g, 143.29 mmol) and 18 g (159.178 mmol) of K2CO3 (freshly dried at 110° C. for 2 hour in a vacuum oven and quickly ground and sieved to 200 mesh). More pyridine (20 ml) followed by copper powder (1.5 g, 10 micron) was added and the mixture was refluxed (oil bath temp 140°-150° C.) for 20 hr under a N2 atmosphere with stirring. The solution was filtered hot, and the residue washed with hot pyridine. The filtrate was concentrated under reduced pressure to give crude 17 (10.5 g) as a foamy solid. The product was purified by chromatography on silia gel using graded methanol/chloroform to give 7.83 g (80% yield from 15) of 17 as a foamy solid.

Workup

  1. customfreshly dried at 110° C. for 2 hour in a vacuum oven and quickly ground
  2. filtrationsieved to 200 mesh)
  3. additionwas added
  4. temperaturethe mixture was refluxed (oil bath temp 140°-150° C.) for 20 hr under a N2 atmosphere
  5. filtrationThe solution was filtered hot
  6. washthe residue washed with hot pyridine
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-573c0ed479784a4c9f0c82f45dd3a15c
Source dataset
uspto-grants-1981_06
Patent number
US04272540

Reaction notes

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