Ethanol → (2-Amino-5-bromo-3-methoxyphenyl)methanol

HRID 475316Notes

Reaction equation

HRID 475316 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([Br:13])=[CH:7][C:3]=1[C:4](O)=[O:5].CCO.O>C1COCC1>[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([Br:13])=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 962WaterHCID 454804572-Amino-5-bromo-3-methoxybenzoic acid

Product 1

HCID 46738297(2-Amino-5-bromo-3-methoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-amino-5-bromo-3-methoxybenzoic acid (20.0 g, 81.30 mmol) is suspended in 250 mL THF, cooled to 0° C. and combined with borane-THF complex (315 mL, 0.315 mol). The reaction mixture is stirred for 5 d at 20° C. and then combined with 10 mL EtOH, stirred for 15 min and then stirred into 250 mL water. The mixture is extracted 3× with DCM, the combined organic phases are dried and the solvent is eliminated in vacuo. The crude product is suspended in DCM and extracted 2× with 400 mL 1 N hydrochloric acid. The combined aqueous phases are adjusted to pH 5-6 with potassium carbonate, the precipitate formed is filtered off and (2-amino-5-bromo-3-methoxy-phenyl)-methanol (HPLC-MS: tRet.=1.41 min, MS(M+H)+=232/234; method FEC3) is obtained.

Workup

  1. stirringstirred for 15 min
  2. extractionThe mixture is extracted 3× with DCM
  3. customthe combined organic phases are dried
  4. extractionextracted 2× with 400 mL 1 N hydrochloric acid
  5. customthe precipitate formed
  6. filtrationis filtered off

Sources & evidence

ORD record
ord-1d642fcfe5fa48daa9ad3998695a57e1
Source dataset
uspto-grants-2014_01
Patent number
US08637549B2

Reaction notes

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