Benzenesulfonic Acid → HCID 57453550, compound

HRID 338212Notes

Reaction equation

HRID 338212 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[C:6]([CH:11]([CH3:13])[CH3:12])[C:5]=1[CH2:14][CH:15]=[O:16])([CH3:3])[CH3:2].[CH2:17]1C(=O)N(Br)C(=O)C1.C1(S(O)(=O)=O)C=CC=CC=1>C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.CN(C=O)C>[CH:1]([C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[C:6]([CH:11]([CH3:12])[CH3:13])[C:5]=1[CH:14]([CH3:17])[CH:15]=[O:16])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 7371Benzenesulfonic AcidHCID 67184N-bromobutanimideHCID 57437669HCID 57437669, compound

Product 1

HCID 57453550HCID 57453550, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 314042,6-Di-tert-butyl-4-methylphenolCatalystHCID 6228DimethylformamideSolvent

Procedure

To a dry DMF solution of 2,6-diisopropyl-4-bromophenylacetaldehyde (7.3 g, 25.8 mmol) at 0° C. was added 2,6-ditert-butyl-4-methylphenol (0.056 g, 0.26 mmol), followed by NBS (4.59 g, 25.8 mmol). After stirring for few minutes, benzenesulfonic acid (8.16 g, 51.6 mmol) was added. The resulting mixture was stirred at 35° C. for 12 h under nitrogen. After regular work up, the crude product was purified by column chromatography to afford 2-(2,6-diisopropyl-4-bromophenyl)propionaldehyde (5.4 g).

Workup

  1. stirringThe resulting mixture was stirred at 35° C. for 12 h under nitrogen
  2. customAfter regular work up, the crude product was purified by column chromatography

Sources & evidence

ORD record
ord-2dec87f3854e4994a08c7d27f2aa0fee
Source dataset
uspto-grants-2014_11
Patent number
US08889864B2

Reaction notes

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