Benzonitrile, 4-bromo- → HCID 21270874, compound

HRID 1193945Notes

Reaction equation

HRID 1193945 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]2[N:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:13][N:12]=2)[CH:7]=[CH:8][C:9]=1Br)([O-:3])=[O:2].BrC1C=CC([C:29]#[N:30])=CC=1.[N+](C1C=C(C=CC=1Br)C#N)([O-])=O>CN1CCCN(C)C1=O>[N+:1]([C:4]1[CH:5]=[C:6]([C:11]2[N:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:13][N:12]=2)[CH:7]=[CH:8][C:9]=1[C:29]#[N:30])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 12162Benzonitrile, 4-bromo-HCID 39268614-Bromo-3-nitrobenzonitrileHCID 21270910HCID 21270910, compound

Product 1

HCID 21270874HCID 21270874, compound

Reagents, catalysts & solvents 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

A mixture of 37.8 g of 2-(3-nitro-4-bromophenyl)-5-n-heptylpyrimidine (obtainable by nitration of 4-bromobenzonitrile, converting the 3-nitro-4-bromobenzonitrile into the corresponding amidine hydrochloride and heating the latter together with n-heptylmalondialdehydtetramethylacetale), 18 g of Cu-(I)-cyanide and 100 ml of 1,3-dimethyltetrahydro-2(1H)pyrimidinon (DMPU) is heated at 150° for 3 hours. After cooling the mixture is filtered, the filtrate and the residue are extracted with methylene chloride and the organic phase is evaporated. 2-(3-Nitro-4-cyanophenyl)-5-n-heptylpyrimidine (F. 73°) is obtained by purification by chromatography. The obtained material is heated together with 33.4 g of CsF in 120 ml of DMPU at 110° for 4 hours. After cooling the mixture is poured onto 600 ml of ice water. After extraction with methylene chloride and purification by chromatography 2-(3-fluoro-4-cyanophenyl)-5-n-heptylpyrimidine (m.p. 43°, clp. 0°, Δε=-37) is obtained

Workup

  1. temperatureis heated at 150° for 3 hours
  2. temperatureAfter cooling the mixture
  3. filtrationis filtered
  4. extractionthe filtrate and the residue are extracted with methylene chloride
  5. customthe organic phase is evaporated

Sources & evidence

ORD record
ord-45c4802d5bc34de6a56adda1529f1173
Source dataset
uspto-grants-1989_03
Patent number
US04812258

Reaction notes

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