Bis(eta-cyclopentadienyl) iron → HCID 178520591, compound

HRID 1824640Notes

Reaction equation

[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][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]>>[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][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])=[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

Reactant 2

HCID 7611Bis(eta-cyclopentadienyl) iron

HCID 1351384716-Bromohexadecanoyl chloride

Product 1

HCID 178520591HCID 178520591, compoundYield 87.1%

Procedure

16-Bromohexadecanoic acid (4.5 g, 14 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 16-bomohexadecanoyl chloride was obtained as a colorless oil and used in the subsequent reaction without further purification. 16-Bromohexadecanoyl chloride (4.5 g, 13 mmol) was treated with ferrocene (2.5 g, 14 mmol) following the same procedure as described for 22 to form a brown oil (5.7 g, 85%): 1H NMR δ 1.25 (s, 22H), 1.68 (m, 2H), 1.84 (m, 2H), 2.68 (m, 2H), 3.39 (m, 2H), 4.18 (s, 5H), 4.47 (A2B2, J=1.5 Hz, 2H), 4.76 (A2B2, J=1.5 Hz, 2H); 13C NMR δ 25.3, 28.8, 29.4, 30.1, 30.2, 30.3, 34.8, 40.4, 70.0, 70.4, 72.7, 89.1, 205.4; FAB-MS obsd 502.1533, calcd exact mass 502.1535 (C26H39BrFeO).

Workup

customused in the subsequent reaction without further purification

Sources & evidence

ORD record: ord-ae0736beaef2431ab86085cc9ca99f43
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07042755B1

Reaction notes

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