Boron tribromide → 4-Thiophen-2-ylphenol

HRID 1837961Notes

Reaction equation

HRID 1837961 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[S:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[C:6]1[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 27694252-(4-methoxyphenyl)thiophene

Product 1

HCID 35641974-Thiophen-2-ylphenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a −78° C. solution of 2-(4-methoxyphenyl)thiophene (0.501 g, 2.64 mmol) in anh. CH2Cl2 (40 mL) was added a solution of BBr3 (1M in CH2Cl2, 6.6 mL, 6.6 mmol), keeping the temperature below −60° C. The reaction mixture was allowed to warm to room temperature and stirred overnight. The resulting mixture cooled to 0° C. and treated with a saturated NaHCO3 solution. After separation the aqueous layer was extracted with CH2Cl2 and EtOAc. The combined organic layers were washed with a saturated NaCl solution, dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography (20% EtOAc/hex) to give 4-(2-thienyl)phenol: TLC (20% EtOAc/hex) Rf 0.29.

Workup

  1. customthe temperature below −60° C
  2. temperatureThe resulting mixture cooled to 0° C.
  3. customAfter separation the aqueous layer
  4. extractionwas extracted with CH2Cl2 and EtOAc
  5. washThe combined organic layers were washed with a saturated NaCl solution
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by flash chromatography (20% EtOAc/hex)

Sources & evidence

ORD record
ord-52866869e3304bc68ee1f66a46db47da
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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