Tetrahydrofuran → 1-Trichlorosilylpyrene

HRID 629845Notes

Reaction equation

[Li]CCCC.Br[C:7]1[C:20]2[C:21]3=[C:22]4[C:17](=[CH:18][CH:19]=2)[CH:16]=[CH:15][CH:14]=[C:13]4[CH:12]=[CH:11][C:10]3=[CH:9][CH:8]=1.C1COCC1.[Si:28](Cl)([Cl:31])([Cl:30])[Cl:29]>C1COCC1.CCOCC>[Cl:29][Si:28]([Cl:31])([Cl:30])[C:7]1[C:20]2[C:21]3=[C:22]4[C:17](=[CH:18][CH:19]=2)[CH:16]=[CH:15][CH:14]=[C:13]4[CH:12]=[CH:11][C:10]3=[CH:9][CH:8]=1

Participants

Conditions

Temperature: -60 °C

Procedure

Under a dry nitrogen atmosphere, n-BuLi (10.6 mL, 1.6 M) in hexanes was added drop-wise to a cooled (−60° C.) solution of 1-bromopyrene (5.01 g, 0.018 mol) in THF/Et2O (1:1) (80 mL) and stirred for 2 hours at −60° C. The solution was cooled to −90° C. and a THF solution of SiCl4 (8.66 g, 0.051 mol) (10 mL) was added slowly and stirred for 24 hours at room temperature. The reaction mixture was evaporated to dryness, washed in Et2O (100 mL), and filtered to remove any unreacted 1-bromopyrene and LiBr. The filtrate was collected and evaporated to dryness to give a 48% yield of 1-trichlorosilylpyrene, a yellow powder. 1HNMR (CDCl3, ppm) 8.66 (d, J=9.3 Hz, 1H), 8.59 (d, J=8.1 Hz, 1H), 8.30 (m, 5H), 8.11 (m, 2H). 13C {1H}NMR (CDCl3, ppm) 136.18 (C), 135.85 (C), 133.13 (CH), 132.06 (C), 131.30 (C), 131.22 CH), 130.31 (CH), 127.96 (CH), 127.67 (CH), 127.61 (CH), 126.65 (CH), 125.61 (C), 125.01 (CH), and 124.39 (C). 29Si{1H} (CDCl3, ppm) −1.64 (s).

Workup

temperatureThe solution was cooled to −90° C.
stirringstirred for 24 hours at room temperature
customThe reaction mixture was evaporated to dryness
washwashed in Et2O (100 mL)
filtrationfiltered
customto remove any unreacted 1-bromopyrene and LiBr
customThe filtrate was collected
customevaporated to dryness

Sources & evidence

ORD record: ord-b9c9f8c5b45b4ca5ae56e729d3fbd116
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315527B2

Reaction notes

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