Methyl 2-amino-5-bromobenzoate → 2-Amino-5-bromobenzenemethanol

HRID 2308225Notes

Reaction equation

HRID 2308225 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:3]=1[C:4](OC)=[O:5].C(O[AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+]>C1COCC1>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 736224Methyl 2-amino-5-bromobenzoateHCID 16684435Lithium tritertbutoxyaluminohydride

Product 1

HCID 110308742-Amino-5-bromobenzenemethanolYield 98.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 13 mmol of methyl 2-amino-5-bromobenzoate in 20 mL of THF at RT was added 65 mmol of 1M lithium tri-tert-butoxyaluminohydride over 10-15 minutes. The solution was heated at reflux for 17 hours. The solution was cooled, poured directly onto silica gel, and eluted with methylene chloride/ethyl acetate; 3:1 followed by 1:1. The product was eluted with 100% methanol to give 2.59 g of the title compound as an off-white solid. MH+: 202; LC: 1.09′.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 17 hours
  3. temperatureThe solution was cooled
  4. additionpoured directly onto silica gel
  5. washeluted with methylene chloride/ethyl acetate
  6. washThe product was eluted with 100% methanol

Sources & evidence

ORD record
ord-da2ee4b907b244a4b2cbb022fd2c7a12
Source dataset
uspto-grants-2004_12
Patent number
US06835737B2

Reaction notes

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