tert-Butanol → tert-Butyl 3-iodobenzoate

HRID 338769Notes

Reaction equation

HRID 338769 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:23](O)([CH3:26])([CH3:25])[CH3:24].N12CCCN=C1CCCCC2>CN(C)C=O.O>[C:23]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([I:1])[CH:3]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 120603-Iodobenzoic acidHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 18386959tert-Butyl 3-iodobenzoateYield 92.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 3-iodobenzoic acid (50 g, 0.2 mol) in N,N-dimethylformamide (250 mL) was added solid 1,1′-carbonyldiimidazole (32.4 g, 0.2 mol) over 15 min. The resulting mixture was heated at 40° C. for 1 hr, then was added tert-butyl alcohol (29.6 g, 0.4 mol) and 1,8-diazabicyclo[5,4,0]undec-7-ene (30.4 g, 0.2 mol) and heated at 40° C. overnight. The reaction was cooled to room temperature, diluted with water (500 mL) and extracted with hexane (2×500 mL). The combined organic layers were washed with water (2×400 mL), brine (250 mL), dried over anhydrous magnesium sulfate (15 g), filtered and concentrated under reduced pressure to give the title compound (56 g, 92%) as an oil. NMR 60 MHz, (CDCl3), δ 8.3 (m, 1H), 7.8 (m, 2H), 7.0 (m, 1H), 1.6 (s, 9H).

Workup

  1. temperatureheated at 40° C. overnight
  2. temperatureThe reaction was cooled to room temperature
  3. extractionextracted with hexane (2×500 mL)
  4. washThe combined organic layers were washed with water (2×400 mL), brine (250 mL)
  5. dry with materialdried over anhydrous magnesium sulfate (15 g)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7b0e1814b54a45b5bb283ceb1ab4f309
Source dataset
uspto-grants-2014_11
Patent number
US08889870B2

Reaction notes

Loading…