Hydrochloric Acid → 1-(4-Bromo-2-fluorophenyl)ethan-1-amine

HRID 1644883Notes

Reaction equation

HRID 1644883 reaction equation
N([CH:4]([NH2:13])[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:6]=1[F:12])=[N+]=[N-].[C:14]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>C1COCC1>[F:12][C:6]1[CH:7]=[C:8]([Br:11])[CH:9]=[CH:10][C:5]=1[CH:4]([NH2:13])[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 86637939C-Azido-C-(2-fluoro-4-bromo-phenyl)-methylamine

Product 1

HCID 185435761-(4-Bromo-2-fluorophenyl)ethan-1-amineYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To C-Azido-C-(2-fluoro-4-bromo-phenyl)-methylamine (0.35 g, 1.43 mmol) was added triphenyl phospine (0.45 g, 1.72 mmol), 2N HCl (2 mL), and THF (2 mL). The reaction mixture was stirred at r.t. for 2 h and the reaction quenched with NaHCO3 (10 mL) and pH adjusted to 8, extracted with dichloromethane (2×30 mL) and washed with brine. The combined organic phases were dried over Na2SO4, filtered and evaporated yielding the crude product. Purification by chromatography (silica, EtOAc/Heptane, 1:1, followed by CH—2Cl2/MeOH 9:1 and with addition of a SCX colon) yielded 93 mg (30%) of 1-(2-Fluoro-4-bromo-phenyl)-ethylamine. 1H NMR δ (CDCl3): 1.44 (3H, d), 2.48 (2H, br s), 4.41 (1H, q), 7.19-7.40 (3H, m).

Workup

  1. customthe reaction quenched with NaHCO3 (10 mL)
  2. extractionextracted with dichloromethane (2×30 mL)
  3. washwashed with brine
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customyielding the crude product
  8. customPurification by chromatography (silica, EtOAc/Heptane, 1:1
  9. additionwith addition of a SCX colon)

Sources & evidence

ORD record
ord-10778dbb663142578a89625890861251
Source dataset
uspto-grants-2012_02
Patent number
US08124634B2

Reaction notes

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