Dimethylformamide → 3-Chloro-4-(1-methylcyclopropyl)-benzaldehyde

HRID 855305Notes

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([CH3:22])[CH2:21][CH2:20]2)=[C:15]([Cl:23])[CH:14]=1.[Li]CCCC.CN(C=O)C>>[Cl:23][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[C:19]1([CH3:22])[CH2:21][CH2:20]1)[CH:8]=[O:9]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 115064744-Cyclopropylbenzaldehyde

HCID 693426514-Bromo-2-chloro-1-(1-methylcyclopropyl)benzene

HCID 178418339Butyllithium

Product 1

HCID 860938233-Chloro-4-(1-methylcyclopropyl)-benzaldehydeYield 63%

Procedure

The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S53) using 4-bromo-2-chloro-1-(1-methylcyclopropyl)-benzene (350 mg, 1.43 mmol), n-BuLi (980 μl, 1.6M solution in hexane, 1.57 mmol) and DMF (443 μl, 5.70 mmol). The isolated residue was purified by flash column chromatography (1:9 ether:pentane) to give 3-chloro-4-(1-methylcyclopropyl)-benzaldehyde (176 mg, 63%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 9.94 (s, 1H), 7.84 (d, J=1.5 Hz, 1H), 7.69 (dd, J=1.5, 8.0 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 1.38 (s, 3H), 0.90-0.80(m, 4H).

Workup

customThe isolated residue was purified by flash column chromatography (1:9 ether:pentane)

Sources & evidence

ORD record: ord-b66e907b60884c64b0c47d61a69b3b44
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259183B2

Reaction notes

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