Hydrochloric Acid → HCID 178419536, compound

HRID 2111473Notes

Reaction equation

HRID 2111473 reaction equation
Cl.[C-:2]1([C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][Br:20])=O)[CH:6]=[CH:5][CH:4]=[CH:3]1.[CH-:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1.[Fe+2:26]>C1(C)C=CC=CC=1>[C-:2]1([CH2:7][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][Br:20])[CH:6]=[CH:5][CH:4]=[CH:3]1.[CH-:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1.[Fe+2:26]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 178520589HCID 178520589, compound

Product 1

HCID 178419536HCID 178419536, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Following a general procedure for preparing 24 (Creager et al. (1994) J. Electroanal. Chem., 370: 203-211), to a freshly prepared zinc/mercury amalgam (6.7 g granulated Zn, 0.4 g HgCl2) in a 100 mL flask was added 10 M HCl (40 mL) with stirring. A solution of 22 (3.0 g, 6.7 mmol) in toluene (40 mL) was added in one portion. The resulting two-phase mixture was heated to reflux and stirred vigorously. After 16 h under reflux, during which two 5 mL portions of 10 M HCl were added, the reaction flask was cooled to rt. The phases were separated, and the organic layer was washed with water (3×100 mL) and dried (MgSO4). The solvent was evaporated in vacuo and the residue was purified by column chromatography (silica, petroleum ether/diethyl ether, 10:1) to afford a brown oil (2.6 g, 90%) that solidified upon standing in the freezer: mp 40-42° C.; 1H NMR δ 1.29 (s, 16H), 1.47 (m, 2H), 1.86 (m, 2H), 2.32 (m, 2H), 3.42 (m, 2H), 4.05 (s, 2H), 4.06 (s, 2H), 4.10 (s, 5H); 13C NMR δ 28.2, 28.8, 29.5, 29.6, 31.1, 32.9, 34.0, 67.0, 68.1, 68.5, 89.6; FAB-MS obsd 432.1114, calcd exact mass 432.1115 (C22H33BrFe).

Workup

  1. customfor preparing 24 (Creager et al. (1994) J. Electroanal. Chem., 370: 203-211)
  2. temperatureThe resulting two-phase mixture was heated
  3. temperatureto reflux
  4. stirringstirred vigorously
  5. additionwere added
  6. customThe phases were separated
  7. washthe organic layer was washed with water (3×100 mL)
  8. dry with materialdried (MgSO4)
  9. customThe solvent was evaporated in vacuo
  10. customthe residue was purified by column chromatography (silica, petroleum ether/diethyl ether, 10:1)

Sources & evidence

ORD record
ord-638ccf1e41174436a943b285182737eb
Source dataset
uspto-grants-2009_04
Patent number
US07518905B2

Reaction notes

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