Boron tribromide → 2-Methylbenzofuran-6-ol

HRID 2076252Notes

Reaction equation

HRID 2076252 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:6]2[CH:7]=[C:8]([CH3:10])[O:9][C:5]=2[CH:4]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:12]=[CH:11][C:6]2[CH:7]=[C:8]([CH3:10])[O:9][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 130130736-Methoxy-2-methylbenzofuran

Product 1

HCID 122034982-Methylbenzofuran-6-olYield 54.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 6-Methoxy-2-methyl-benzofuran 125-A (1.76 g, 10.85 mmol) in 45 ml of CH2Cl2 at −5° C. was added BBr3 (24 ml of 1M BBr3 in CH2Cl2, 16.28 mmol). The reaction was allowed to warm to 0° C. and stirred at that temperature for 1.5 hr. The reaction was poured into a mixture of ice and saturated aqueous NaHCO3 and layers were separated. The aqueous layer was re-extracted with CH2Cl2. The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to a brown oil. The residue was chromatographed on silica gel eluting CH2Cl2 to give 872 mg (54%) of 6-Hydroxy-2-methyl-benzofuran 125-B. Anal calc'd for C9H8O2: C, 72.96; H, 5.44. Found: C, 72.72; H, 5.43.

Workup

  1. customwere separated
  2. extractionThe aqueous layer was re-extracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure to a brown oil
  5. customThe residue was chromatographed on silica gel
  6. washeluting CH2Cl2

Sources & evidence

ORD record
ord-aa59aed52a5f437995ff6196feb0dc36
Source dataset
uspto-grants-2011_04
Patent number
US07923457B2

Reaction notes

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