Dimethylformamide → 2,6-Diisopropyl-4-bromobenzaldehyde

HRID 338210Notes

Reaction equation

HRID 338210 reaction equation
I[C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[CH:6][C:5]([Br:11])=[CH:4][C:3]=1[CH:12]([CH3:14])[CH3:13].[Li]CCCC.CN([CH:23]=[O:24])C>C1(C)C=CC=CC=1>[CH:12]([C:3]1[CH:4]=[C:5]([Br:11])[CH:6]=[C:7]([CH:8]([CH3:10])[CH3:9])[C:2]=1[CH:23]=[O:24])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 574376675-Bromo-2-iodo-1,3-diisopropylbenzeneHCID 178418339Butyllithium

Product 1

HCID 574376682,6-Diisopropyl-4-bromobenzaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A 150 mL of dry toluene solution of 1-iodo-2,6-diisopropyl-4-bromobenzene (17.6 g, 0.048 mol) was treated with n-BuLi (1.6 M in hexane, 75 mL) at −78° C. in 30 minutes. After stirring for 15 minutes, dry DMF (20 mL) in 50 mL of toluene was added dropwise. The resulting mixture was slowly warmed up to room temperature. After regular work up, the crude product was distilled at 140° C. under vacuum to afford 2,6-diisopropyl-4-bromobenzaldehyde (11.5 g).

Workup

  1. distillationAfter regular work up, the crude product was distilled at 140° C. under vacuum

Sources & evidence

ORD record
ord-92f6288e6b3842dd9f76fc58992d3efd
Source dataset
uspto-grants-2014_11
Patent number
US08889864B2

Reaction notes

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