tert-Butanol → HCID 66816641, compound

HRID 1755073

Reaction equation

HRID 1755073 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.[Br:17][C:18]1[C:26]([CH3:27])=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][C:19]=1[CH3:28]>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([O:5][C:22](=[O:23])[C:21]1[CH:25]=[C:26]([CH3:27])[C:18]([Br:17])=[C:19]([CH3:28])[CH:20]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 179371424-Bromo-3,5-dimethylbenzoic acid

Product 1

HCID 66816641HCID 66816641, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Dehydrated tert-butanol (0.19 ml, 2.0 mmol), 4-dimethylaminopyridine (81 mg, 0.67 mmol) and EDCI (255 mg, 1.33 mmol) were added to a solution of 4-bromo-3,5-dimethyl-benzoic acid (123 mg, 0.535 mmol) in dichloromethane (1.0 ml) at 0° C., and the mixture was stirred at room temperature for 25 hours. The reaction mixture was diluted with dichloromethane, and the organic layer was washed with water, dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/1→50/1) to give 4-bromo-3,5-dimethyl-benzoic acid tert-butyl ester (106 mg, 70%).

Workup

  1. washthe organic layer was washed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/1→50/1)

Sources & evidence

ORD record
ord-fa5c856f9a334d85926eeed27de47450
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Linked notes

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