Isopropyl iodide → Methyl 3-bromo-4-isopropoxybenzoate

HRID 1820958Notes

Reaction equation

HRID 1820958 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].I[CH:14]([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:14]([CH3:16])[CH3:15])[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 4778958Methyl 3-bromo-4-hydroxybenzoate

Product 1

HCID 21956810Methyl 3-bromo-4-isopropoxybenzoateYield 79.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 4.6 g (19.9 mmol) of methyl 3-bromo-4-hydroxybenzoate (from Step A), 2.2 mL (21.9 mmol) of 2-iodopropane and 5.5 g (39.8 mmol) of potassium carbonate in 10 mL of DMF was stirred at 65° C. for 3 h. The mixture was diluted with 20 mL of EtOAc and washed with sat'd NaCl, H2O (3×), and sat'd NaCl. The organic layer was dried over MgSO4 and concentrated. Chromatography on a Biotage 40M cartridge using 24:1 v/v hexanes/EtOAc gave 4.3 g of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.44 (d, J=6.2, 6H), 3.91 (s, 3H), 4.71-4.79 (m, 1H), 6.99 (d, J=8.9, 1H), 8.18 (dd, J=2.2, 8.8, 1H), 8.24 (d, J=2.1, 1H).

Workup

  1. washwashed with sat'd NaCl, H2O (3×)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-373d3a46d1104831859acacff52ef819
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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