Methyl iodide → HCID 86761594, compound

HRID 1517551Notes

Reaction equation

HRID 1517551 reaction equation
[Br:1][C:2]1[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:8]=[C:7]([Br:16])[C:3]=1[C:4]([OH:6])=[O:5].[C:17]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[Br:1][C:2]1[C:10]([O:11][CH3:17])=[C:9]([C:12]([CH3:13])([CH3:15])[CH3:14])[CH:8]=[C:7]([Br:16])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86761592HCID 86761592, compound

Product 1

HCID 86761594HCID 86761594, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

step 4—To a solution of 122 (1.0 eq, 2.18 mmol, 767 mg) in acetone (15 mL) was added K2CO3 (3.0 eq, 6.54 mmol, 903 mg) and MeI (5.0 eq, 10.89 mmol, 680 μL). The mixture was heated at 60° C. for 2 h before it was cooled to RT and the organic volatiles were removed under reduced pressure. The residue was partitioned between in EtOAc and water. The organic layer was separated, washed with brine, dried and concentrated. The crude was purified by SiO2 chromatography eluting with a EtOAc/hexane gradient (5 to 30% EtOAc) to afford 278 mg of 2,6-dibromo-4-tert-butyl-3-methoxybenzoic acid (124).

Workup

  1. temperaturewas cooled to RT
  2. customthe organic volatiles were removed under reduced pressure
  3. customThe residue was partitioned between in EtOAc and water
  4. customThe organic layer was separated
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe crude was purified by SiO2 chromatography
  9. washeluting with a EtOAc/hexane gradient (5 to 30% EtOAc)

Sources & evidence

ORD record
ord-85168d066a414d9bb8958e3fcdcc9560
Source dataset
uspto-grants-2012_07
Patent number
US08232271B2

Reaction notes

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