Bromine → 6-bromo-3,4-dihydro-2H-1-benzopyran-4-amine

HRID 747038Notes

Reaction equation

HRID 747038 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([NH2:11])[CH2:3][CH2:2]1.[Br:12]Br>CC(O)=O>[Br:12][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[O:1][CH2:2][CH2:3][CH:4]2[NH2:11]

Participants

4

Reactant 2

HCID 24408BromineHCID 49619573,4-Dihydro-2H-1-benzopyran-4-amine

Product 1

HCID 162444146-bromo-3,4-dihydro-2H-1-benzopyran-4-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of chroman-4-ylamine (2.550 g, 17.09 mmol) in AcOH (50 mL) at RT was treated with Br2 (3.01 g, 0.96 mL, 18.8 mmol) drop-wise. The reaction was stirred at RT until HPLC analysis showed complete consumption of starting material. The mixture was diluted with H2O (100 mL) and NaOH was added until the solution became basic. The aqueous layer was extracted with EtOAc until TLC analysis of the aqueous layer showed no evidence of the title compound. The combined organics were dried over MgSO4 and concentrated in vacuo to yield the crude compound, which was purified by flash column chromatography to afford the pure title compound. MS (APCI pos) 229 (M+H).

Workup

  1. customconsumption of starting material
  2. additionThe mixture was diluted with H2O (100 mL) and NaOH
  3. additionwas added until the solution
  4. extractionThe aqueous layer was extracted with EtOAc until TLC analysis of the aqueous layer
  5. dry with materialThe combined organics were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto yield the crude compound, which
  8. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-059f5e6aa2fa4194871b66ae3a6859a7
Source dataset
uspto-grants-2008_07
Patent number
US07393852B2

Reaction notes

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