Hydrochloric Acid → HCID 17839508, compound

HRID 600137Notes

Reaction equation

HRID 600137 reaction equation
C([Li])CCC.[CH2:6]([C:12]1[C:17]([CH2:18][CH2:19][CH3:20])=[C:16]([CH2:21][CH2:22][CH3:23])[C:15]([CH2:24][CH2:25][CH3:26])=[C:14]([CH2:27][CH2:28][CH3:29])[C:13]=1[CH2:30][C:31]#[C:32][CH2:33][CH2:34][CH3:35])[C:7]#[C:8][CH2:9][CH2:10][CH3:11].I[C:37]1[CH:42]=[CH:41][C:40](I)=[C:39]([I:44])[C:38]=1[I:45].CN1C(=O)N(C)CCC1.Cl>Cl[Cu].C1COCC1>[I:44][C:39]1[C:38]([I:45])=[CH:37][C:42]2[C:41](=[C:8]([CH2:9][CH2:10][CH3:11])[C:7]3[CH2:6][C:12]4[C:13]([CH2:30][C:31]=3[C:32]=2[CH2:33][CH2:34][CH3:35])=[C:14]([CH2:27][CH2:28][CH3:29])[C:15]([CH2:24][CH2:25][CH3:26])=[C:16]([CH2:21][CH2:22][CH3:23])[C:17]=4[CH2:18][CH2:19][CH3:20])[CH:40]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 124651,2,3,4-TETRAIODOBENZENEHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 11188975HCID 11188975, compoundHCID 178418339Butyllithium

Product 1

HCID 17839508HCID 17839508, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

n-Butyl lithium (3.0 ml, 4.8 mmols, 1.6mol/l) was added to a THF solution (20 ml) of Cp2ZrCl2 (0.702 g, 2.4 mmols) at −78° C. After the mixture was stirred for an hour, 1,2-bis(2-hexynyl)-3,4,5,6-tetrapropylbenzene (0.813 g, 2.0 mmols) was added to the mixture. A cooling bath was withdrawn, and the mixture was stirred for an hour. Tetraiodobenzene (1.16 g, 2.0 mmols), DMPU (0.73 ml, 6.0 mmols) and CuCl (0.416 g, 4.2 mmols) were added to the mixture. After stirring for an hour at 50° C., 3N HCl was added to terminate the reaction. The reaction mixture was extracted with chloroform. The extract was then washed with sodium hydrogencarbonate aqueous solution and brine. After the pressure was reduced, column chromatography was performed using silica gel as the packing material to give the title compound (0.477 g) as a pink solid. The isolation yield was 33%

Workup

  1. customA cooling bath was withdrawn
  2. stirringthe mixture was stirred for an hour
  3. stirringAfter stirring for an hour at 50° C.
  4. customto terminate
  5. customthe reaction
  6. extractionThe reaction mixture was extracted with chloroform
  7. washThe extract was then washed with sodium hydrogencarbonate aqueous solution and brine

Sources & evidence

ORD record
ord-9bb45d2519f84d519acd027e06a1fbe1
Source dataset
uspto-grants-2011_03
Patent number
US07901594B2

Reaction notes

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