Dimethylformamide → 4-(1-Fluorocyclobutyl)benzaldehyde

HRID 19768Notes

Reaction equation

C1(C2C=CC([CH:8]=[O:9])=CC=2)CC1.Br[C:13]1[CH:18]=[CH:17][C:16]([C:19]2([F:23])[CH2:22][CH2:21][CH2:20]2)=[CH:15][CH:14]=1.[Li]CCCC.CCCCCC.CN(C=O)C>>[F:23][C:19]1([C:16]2[CH:17]=[CH:18][C:13]([CH:8]=[O:9])=[CH:14][CH:15]=2)[CH2:22][CH2:21][CH2:20]1

Participants

Reactant 5

HCID 6228Dimethylformamide

HCID 8058Hexane

HCID 115064744-Cyclopropylbenzaldehyde

HCID 685641591-Bromo-4-(1-fluorocyclobutyl)benzene

HCID 178418339Butyllithium

Product 1

HCID 847180204-(1-Fluorocyclobutyl)benzaldehyde

Procedure

The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S1-A) using 1.64 g of 1-bromo-4-(1-fluoro-cyclobutyl)-benzene (7.16 mmol), 4.92 ml of a 1.6 molar solution of n-BuLi in hexane (7.87 mmol) and 1.1 ml of DMF (14.32 mmol). 4-(1-Fluoro-cyclobutyl)-benzaldehyde was isolated as crude product as a light yellow liquid (1.23 g, 96%). 1H NMR (CDCl3, 300 MHz): δ 1.84 (m, 1H), 2.15 (m, 1H), 2.49-2.81 (m, 5H), 7.63 (d, J=8 Hz, 2H), 7.92 (d, J=8 Hz, 2H), 10.03 (s, 1H).

Sources & evidence

ORD record: ord-bb6f4adb33084144b99c3ec8cb6c4e5d
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745477B2

Reaction notes

Loading…