Trifluoroacetic acid → 3-Bromo-4-(3-chlorobenzyl)thiophene

HRID 870040Notes

Reaction equation

HRID 870040 reaction equation
[Br:1][C:2]1[C:3]([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)O)=[CH:4][S:5][CH:6]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[C:3]([CH2:7][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)=[CH:4][S:5][CH:6]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 45140393(4-Bromo-3-thienyl)(3-chlorophenyl)methanol

Product 1

HCID 451405813-Bromo-4-(3-chlorobenzyl)thiophene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (4-bromo-3-thienyl)(3-chlorophenyl)methanol from Example 3, Step 1 (144 mg, 0.474 mmol) in CH2Cl2 (1 mL) at 0° C., were successively added triethylsilane (303 μL, 1.90 mmol), quickly and TFA (364 μL, 4.74 mmol) dropwise. After 30 min., the reaction was concentrated to dryness and the residue was dissovled in CHCl3 and washed with 5% aq. NaHCO3. The aqueous layer was extracted with CHCl3 and the combined organics were washed with water and brine, dried (Na2SO4) and concentrated. The crude product was purified on silica gel (toluene/hexane 5:95) to afford the desired product as a colorless oil.

Workup

  1. customat 0° C.
  2. concentrationthe reaction was concentrated to dryness
  3. washwashed with 5% aq. NaHCO3
  4. extractionThe aqueous layer was extracted with CHCl3
  5. washthe combined organics were washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude product was purified on silica gel (toluene/hexane 5:95)

Sources & evidence

ORD record
ord-c279ba4439144fbfac463b20fac3598e
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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