tert-Butanol → 1,1-Dimethylethyl 3-bromo-5-iodobenzoate

HRID 269556

Reaction equation

HRID 269556 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5]([OH:7])=[O:6].Cl.CN(C)CCCC(N=C=N)C.[C:24](O)([CH3:27])([CH3:26])[CH3:25]>CN(C)C1C=CN=CC=1.ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5]([O:7][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:6]

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 51825203-Bromo-5-iodobenzoic acidHCID 219829211-(3-Dimethylaminopropyl)ethylcarbodiimide hydrochloride

Product 1

HCID 574859731,1-Dimethylethyl 3-bromo-5-iodobenzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-bromo-5-iodobenzoic acid (50 g, 153 mmol), 1-(3-dimethylaminopropyl)-ethylcarbodiimide hydrochloride (30.8 g, 153 mmol), 4-dimethylaminopyridine (18.6 g, 153 mmol) and t-butanol (69.4 g, 90 ml, 153 mmol) in dichloromethane (500 ml) was stirred at room temperature overnight. The reaction mixture was washed with 2MHCl and saturated NaHCO3. The organic phase was dried and evaporated to give the title compound as a light brown solid. (48 g; 85%).

Workup

  1. washThe reaction mixture was washed with 2MHCl and saturated NaHCO3
  2. customThe organic phase was dried
  3. customevaporated

Sources & evidence

ORD record
ord-9d41c9fb650b4654bde723322a0a2f97
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Linked notes

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