1-Bromo-4-fluorobenzene → Tributyl(4-fluorophenyl)stannane

HRID 571434Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[Li]C(C)(C)C.[Sn:14](Cl)([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH2:17][CH3:18]>CCOCC>[CH2:23]([Sn:14]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:19][CH2:20][CH2:21][CH3:22])[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1)[CH2:24][CH2:25][CH3:26]

Participants

Conditions

Temperature: 23 °C

Procedure

To 1-bromo-4-fluorobenzene (1.75 g, 10.0 mmol, 1.00 equiv) in Et2O (25 mL) at −78° C. was added tBuLi (1.7 M in pentane, 11.8 mL, 20 mmol, 2.0 equiv). The reaction mixture was stirred at −78° C. for 30 min before the addition of nBu3SnCl (3.26 g, 10.0 mmol, 1.00 equiv). The reaction mixture was warmed to 23° C. and stirred for 1.0 hr before being filtered through a plug of neutral alumina. The filtrate was concentrated in vacuo to afford 3.76 g of the title compound as a colorless oil (98% yield).

Workup

filtrationbefore being filtered through a plug of neutral alumina
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-389224d3bc6e4b6388f06a1646998a87
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024093B2

Reaction notes

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