Benzyl Alcohol → Benzyl 2-amino-3-iodobenzoate

HRID 1851406Notes

Reaction equation

HRID 1851406 reaction equation
[NH2:1][C:2]1[C:10]([I:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O.C1(C)C=CC=CC=1>[NH2:1][C:2]1[C:10]([I:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:5]

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2820702-Amino-3-iodobenzoic acid

Product 1

HCID 57901768Benzyl 2-amino-3-iodobenzoateYield 83%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-3-iodobenzoic acid (5.00 g), benzyl alcohol (2.17 mL) and triphenylphosphine (7.97 g) in tetrahydrofuran (76 mL) was added a 40% toluene solution (13.2 g) of diethyl azodicarboxylate, and the mixture was stirred at room temperature for 0.5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-15:85) to give the title compound (5.56 g, yield 83%) as an orange oil. MS m/z 354 (M+H+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-15:85)

Sources & evidence

ORD record
ord-8d3e21214a15490297bcfe5fe57c387b
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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