Water → HCID 178520589, compound

HRID 2111471Notes

Reaction equation

HRID 2111471 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Br:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](Cl)=[O:18].[CH-:20]1[CH:24]=[CH:23][CH:22]=[CH:21]1.[CH-:25]1[CH:29]=[CH:28][CH:27]=[CH:26]1.[Fe+2:30].O>C(Cl)Cl>[C-:20]1([C:17]([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][Br:5])=[O:18])[CH:24]=[CH:23][CH:22]=[CH:21]1.[CH-:25]1[CH:29]=[CH:28][CH:27]=[CH:26]1.[Fe+2:30]

Participants

6

Reactant 4

HCID 962WaterHCID 7611Bis(eta-cyclopentadienyl) ironHCID 6451240Aluminum(III) ChlorideHCID 1230700612-bromododecanoyl chloride

Product 1

HCID 178520589HCID 178520589, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Following a general procedure for preparing 21 (Creager et al. (1994) J. Electroanal. Chem., 370: 203-211), a solution of 12-bromododecanoic acid (4.2 g, 15 mmol) in SOCl2 (50 mL) was heated at 50° C. under argon for 1 h. The excess SOCl2 was removed by water pump distillation with benzene (3×50 mL). 4.3 g (95%) of 12-bromododecanoyl chloride was obtained as a colorless oil and used in the subsequent reaction without further purification. In a 50 mL flask anhydrous AlCl3 (2.8 g, 21 mmol) was added to a stirred solution of 12-bromododecanoyl chloride (4.0 g, 13.6 mmol) in dry CH2Cl2 (30 mL) at 0° C. under argon for 20 min. Then the mixture was added dropwise over 10 min to a solution of ferrocene (2.6 g, 14 mmol) in CH2Cl2 (50 mL) at 0° C. The mixture was stirred and allowed to warm to rt. After 2 h water (30 mL) was added slowly into this mixture. Then the phases were separated, and the organic layer was washed with water (3×100 mL) and NaHCO3 (2×50 mL) and over (MgSO4). The solvent was evaporated in vacuo and the residue was purified by column chromatography (silica, petroleum ether/diethyl ether, 10:3) to afford a red oil (4.3 g, 85%). 1H NMR δ 1.28 (s, 16H), 1.64 (m, 2H), 2.63 (m, 2H), 3.29 (m, 2H), 4.19 (s, 5H), 4.48 (A2B2, J=1.5 Hz, 2H), 4.78 (A2B2, J=1.5 Hz, 2H); 13C NMR δ 25.0, 28.5, 29.0, 30.1, 30.9, 33.3, 34.5, 40.5, 70.0, 70.4, 72.9, 89.0, 205.0; FAB-MS obsd 446.0955, calcd exact mass 446.0958 (C12H31.BrFeO).

Workup

  1. customused in the subsequent reaction without further purification
  2. customThen the phases were separated
  3. washthe organic layer was washed with water (3×100 mL) and NaHCO3 (2×50 mL) and over (MgSO4)
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by column chromatography (silica, petroleum ether/diethyl ether, 10:3)

Sources & evidence

ORD record
ord-c4d9dd4f5ef64846ba011297f826d882
Source dataset
uspto-grants-2009_04
Patent number
US07518905B2

Reaction notes

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