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Sulfuric Acid → Tert-butyl 2-bromo-4-methylpentanoate

HRID 636755
Notes
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Reaction equation

HRID 636755 reaction equation
[Br:1][CH:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3]([OH:5])=[O:4].S(=O)(=O)(O)O.[CH2:15]=[C:16]([CH3:18])[CH3:17]>ClCCl>[Br:1][CH:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3]([O:5][C:16]([CH3:18])([CH3:17])[CH3:15])=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 1426812-Bromo-4-methylpentanoic acid

Product 1

HCID 11276775Tert-butyl 2-bromo-4-methylpentanoateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

The product from Step 1 above (63.3 g, 0.32 mol) was dissolved in dichloromethane (250 mL), concentrated sulfuric acid (2 mL) was added, and cooled to −40° C. in a pressure bottle. Isobutene was condensed into the solution to roughly double the volume, and the mixture was then allowed to warm to room temperature overnight. Following evaporation to half of the volume under reduced pressure, the solution was washed with 10% aqueous sodium bicarbonate, dried over Na2SO4, and thoroughly evaporated under reduced pressure at room temperature to leave the title compound as a yellow oil (79.9 g, 0.314 mol; 98%).

Workup

  1. customcondensed into the solution
  2. temperatureto warm to room temperature overnight
  3. customevaporation to half of the volume under reduced pressure
  4. washthe solution was washed with 10% aqueous sodium bicarbonate
  5. dry with materialdried over Na2SO4
  6. customthoroughly evaporated under reduced pressure at room temperature

Sources & evidence

ORD record
ord-315b50be6d1e4a19b8525ca5a9ac861c
Source dataset
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06194451B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes