Tetrahydrofuran → 2-(2-Amino-4-bromophenyl)propan-2-ol

HRID 2209288Notes

Reaction equation

HRID 2209288 reaction equation
C(O[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:6]=1[NH2:12])(=O)C.[CH3:13][Mg+].[Br-].[CH2:16]1[CH2:20][O:19]CC1>>[NH2:12][C:6]1[CH:7]=[C:8]([Br:11])[CH:9]=[CH:10][C:5]=1[C:20]([OH:19])([CH3:16])[CH3:13]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 1178436442-Amino-4-bromophenyl acetateHCID 178418689HCID 178418689, compound

Product 1

HCID 571557062-(2-Amino-4-bromophenyl)propan-2-ol

Procedure

Into the solution of 2-amino-4-bromophenyl acetate (2.3 g) in THF (50 mL) was added 1M solution of MeMgBr in THF (50 mL) at 0° C. Then the reaction mixture was warmed to rt., and stirred for another 2 h. The reaction was quenched by saturated NH4Cl water solution, and extracted with ethyl acetate and washed with brine, after being dried, the solvent was removed to provide 2.3 g crude of 2-(2-amino-4-bromophenyl)propan-2-ol. This product was used in the next step reaction without any purification. LCMS [M+H]+: 231.86. 1H NMR (400 MHz, Chloroform-d) δ 7.26 (s, 1H), 6.95 (d, J=8.1 Hz, 2H), 6.81-6.73 (m, 3H), 1.64 (s, 6H).

Workup

  1. customThe reaction was quenched by saturated NH4Cl water solution
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. customafter being dried
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-1dc8bd9f19f444479e58a7db0303367b
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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