Dimethylformamide → HCID 22259691, compound

HRID 855317Notes

Reaction equation

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

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 115064744-Cyclopropylbenzaldehyde

HCID 595965124-Bromo-1-tert-butyl-2-chlorobenzene

HCID 178418339Butyllithium

Product 1

HCID 22259691HCID 22259691, compoundYield 82%

Procedure

The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S53) using 4-bromo-1-tert-butyl-2-chloro-benzene (200 mg, 0.81 mmol), nBuLi (0.66 ml, 1.6M solution in hexane, 1.05 mmol) and DMF (251 μl, 3.23 mmol). The isolated residue was purified by flash column chromatography (1:9 ether:pentane) to give 4-tert-butyl-3-chloro-benzaldehyde (130 mg, 82%) as a colorless liquid. 1H NMR (CDCl3, 300 MHz): δ 9.94 (s, 1H), 7.85 (d, J=2 Hz, 1H), 7.70 (dd, J=2 and 8 Hz, 1H), 7.60 (d, J=8.0 Hz, 1H), 1.51 (s, 9H).

Workup

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

Sources & evidence

ORD record: ord-5041c2ae980145c2baa2c3f762bc3b54
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259183B2

Reaction notes

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