Isopropyl iodide → Methyl 3-bromo-5-isopropoxybenzoate

HRID 1051065Notes

Reaction equation

HRID 1051065 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C([O-])([O-])=O.[K+].[K+].I[CH:20]([CH3:22])[CH3:21]>CN(C=O)C.CC(=O)OCC>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH:20]([CH3:22])[CH3:21])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 53216607Methyl 3-bromo-5-hydroxybenzoate

Product 1

HCID 53216693Methyl 3-bromo-5-isopropoxybenzoateYield 75%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a flask containing methyl 3-bromo-5-hydroxybenzoate (2.1 g, 8.9 mmol) in anhydrous DMF (10 mL) was added K2CO3 (2.47 g, 17.9 mmol) and 2-iodopropane (1.07 mL, 10.7 mmol). The reaction mixture was heated at 65° C. overnight then diluted with EA and washed with NaHCO3. The organic layers were dried and concentrated to provide 1.81 g (75%) of methyl 3-bromo-5-isopropoxybenzoate as a white solid. LCMS-ESI (m/z) calculated for C11H13BrO3: 273.12; no observed m/z ion, tR=4.17 min.

Workup

  1. washwashed with NaHCO3
  2. customThe organic layers were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4b6f3a74fc0849bd9ed54357bce1a402
Source dataset
uspto-grants-2016_07
Patent number
US09388147B2

Reaction notes

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