Borane → 1192474-21-7

HRID 541931Notes

Reaction equation

HRID 541931 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:10]=1)[C:5](O)=[O:6].B>O1CCCC1>[Br:1][C:2]1[CH:10]=[C:9]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])[CH:8]=[C:4]([CH2:5][OH:6])[CH:3]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 57962321HCID 57962321, compound

Product 1

HCID 579619961192474-21-7

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 3-bromo-5-[(tert-butoxycarbonyl)amino]benzoic acid (13.6 g, 43.1 mol) in tetrahydrofuran (44 mL) at 0° C. was treated with 1 M borane in THF (64.6 mL, 64.6 mmol) dropwise and stirred at 20° C. for 1 h. The reaction mixture was concentrated, diluted with ethyl acetate (200 mL), and washed with 1 M HCl (100 mL) and brine (50 mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered, and evaporated to give the desired product as a colorless oil that was used without further purification. LCMS for C12H16BrNO3Na (M+Na)+: m/z=323.9, 325.9.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate (200 mL)
  3. washwashed with 1 M HCl (100 mL) and brine (50 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-93fbf99d6dd94f9fa9d1601b5d3004eb
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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