Dimethylformamide → HCID 86093855, compound

HRID 855332Notes

Reaction equation

HRID 855332 reaction equation
C1(C2C=CC([CH:8]=[O:9])=CC=2)CC1.Br[C:13]1[CH:18]=[CH:17][C:16]([C:19]([O:22][CH3:23])([CH3:21])[CH3:20])=[C:15]([Cl:24])[CH:14]=1.[Li]CCCC.CCCCCC.CN(C=O)C>>[Cl:24][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[C:19]([O:22][CH3:23])([CH3:21])[CH3:20])[CH:8]=[O:9]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8058HexaneHCID 115064744-CyclopropylbenzaldehydeHCID 69342974HCID 69342974, compoundHCID 178418339Butyllithium

Product 1

HCID 86093855HCID 86093855, compoundYield 62%

Procedure

The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S53) using 310 mg of 4-bromo-2-chloro-1-(1-methoxy-1-methyl-ethyl)-benzene (1.18 mmol), 1.1 ml of a 1.6 molar solution of n-BuLi in hexane (1.76 mmol) and 457 μl of DMF (5.88 mmol). The isolated residue was purified by flash column chromatography (1:9 ether/pentane) to give 154 mg of 3-chloro-4-(1-methoxy-1-methyl-ethyl)-benzaldehyde (62%) as a colorless liquid. 1H NMR (CDCl3, 300 MHz): δ 1.69 (s, 6H), 3.18 (s, 3H), 7.69 (d, J=8.2 Hz, 1H), 7.75 (dd, J=8.2 and 1.7 Hz, 1H), 7.58 (d, J=1.7 Hz, 1H), 9.97 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-7bcb2dec82b74680921815665289e44a
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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