Methanol → 2-Amino-5-iodobenzenemethanol

HRID 986020Notes

Reaction equation

HRID 986020 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13](=O)[C:14]1[CH:19]=[C:18]([I:20])[CH:17]=[CH:16][C:15]=1[NH2:21].CO.C(OCC)(=O)C>C1COCC1>[NH2:21][C:15]1[CH:16]=[CH:17][C:18]([I:20])=[CH:19][C:14]=1[CH2:13][OH:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 847811Methyl 2-amino-5-iodobenzoateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 142210292-Amino-5-iodobenzenemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diisobutylaluminium hydride (210 cm3 of a 1.5M solution in THF) was added at -30° to a stirred solution of methyl-2-amino-5-iodobenzoate (28.0 g) in THF (100 cm3) under nitrogen. The mixture was warmed to room temperature, stirred for 16 hours and treated with methanol (35 cm3). Ethyl acetate (500 cm3) was added and the mixture filtered to remove inorganic material. The filtrate was concentrated in vacuo to afford a solid which was chromatographed on silica (Merck "MK 60.9385") eluting wiht chloroform:methanol, 49:1 (by volume), and the requisite fractions were combined and evaporated in vacuo to give 2-amino-5-iodobenzyl alcohol, m.p. 125°, (19.0 g).

Workup

  1. filtrationthe mixture filtered
  2. customto remove inorganic material
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto afford a solid which
  5. customwas chromatographed on silica (Merck "MK 60.9385")
  6. washeluting wiht chloroform
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-617038662c0741b6bc8c4612cc59c849
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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