Carbon tetrabromide → HCID 19852273, compound

HRID 1607234Notes

Reaction equation

HRID 1607234 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].[F:25][C:26]([F:53])([F:52])[O:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35]([N:37]2[CH2:41][C:40]([CH:43]=O)([CH3:42])[C:39]([C:45]3[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][CH:46]=3)=[N:38]2)=[O:36])=[CH:30][CH:29]=1>C(Cl)Cl.[Zn]>[F:53][C:26]([F:25])([F:52])[O:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35]([N:37]2[CH2:41][C:40]([CH:42]=[C:20]([Br:24])[Br:21])([CH3:43])[C:39]([C:45]3[CH:46]=[CH:47][C:48]([Cl:51])=[CH:49][CH:50]=3)=[N:38]2)=[O:36])=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 19852111HCID 19852111, compound

Product 1

HCID 19852273HCID 19852273, compoundYield 48.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To 1.5 g of zinc dust (23.8 mmole) and 5.2 g of triphenylphosphine (20 mmole) in 20 ml of methylene chloride was added 6.8 g of carbon tetrabromide (20 mmole) after stiring for 90 minutes a solution of 3 g of N-(4-trifluoromethoxyphenyl)-3-(4-chlorophenyl)-4-formyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide in 10 ml of MeCl2 is added and the mixture is stirred an additional 60 minutes. The reaction is partitioned between ether and aqueous sodium thiosulfate, dried, rotovaped and chromatographed (ether/hexane) to yield 2.0 g of N-(4-trifluoromethoxyphenyl)-3-(4-chlorophenyl)-4-(2,2-dibromovinyl)-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide an oil. NMR data was consistent with the structure.

Workup

  1. customThe reaction is partitioned between ether and aqueous sodium thiosulfate
  2. customdried
  3. customchromatographed (ether/hexane)

Sources & evidence

ORD record
ord-da26178f104d4b1680d32c84eff3e969
Source dataset
uspto-grants-1989_09
Patent number
US04863947

Reaction notes

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