Hydrochloric Acid → 2-(4-Bromophenyl)thiophen-3-amine

HRID 1990064Notes

Reaction equation

HRID 1990064 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:12]=[CH:11][S:10][C:9]=1[C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=1)(C)(C)C.Cl.O.C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([C:9]2[S:10][CH:11]=[CH:12][C:8]=2[NH2:7])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 57975436tert-Butyl [2-(4-bromophenyl)thiophen-3-yl]carbamate

Product 1

HCID 534219992-(4-Bromophenyl)thiophen-3-amine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Treat a solution of [2-(4-bromo-phenyl)-thiophen-3-yl]-carbamic acid tert-butyl ester (10.8 g, 0.3 mol) in Ethyl acetate (75 mL) at 0° C., dropwise with 244 mL (8 mL/mmol) of freshly prepared 1N HCl in Ethyl acetate and stir the mixture at r.t. overnight. Dissolve the white precipitate with H2O (100 mL) and neutralize with a NaHCO3 saturated solution. Extract the mixture with Ethyl acetate (3×100 mL) and dry the combined organics and concentrate to give a slightly colored solid. Purification by flash chromatography (Silica gel-Hexane/Ethyl acetate 49:1 then 9:1) furnishes 5.7 g (74%, at 1.0 g scale, the reaction was quantitative) of title compound as a pale yellow solid.

Workup

  1. extractionExtract the mixture with Ethyl acetate (3×100 mL)
  2. customdry the combined organics and
  3. concentrationconcentrate
  4. customto give a slightly colored solid
  5. customPurification by flash chromatography (Silica gel-Hexane/Ethyl acetate 49:1
  6. custom9:1) furnishes 5.7 g (74%

Sources & evidence

ORD record
ord-49001e120cf04324a60ba040d137f948
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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