Boron tribromide → [1,1'-Biphenyl]-3,3',5-triol

HRID 1375681Notes

Reaction equation

HRID 1375681 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17]C)[CH:12]=2)[CH:6]=[C:7]([O:9]C)[CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)[CH:6]=[C:7]([OH:9])[CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57321084HCID 57321084, compound

Product 1

HCID 88736[1,1'-Biphenyl]-3,3',5-triolYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 395 mg (1.62 mmol) of 3,5,3′-trimethoxybiphenyl was added 9 mL of 1.0 M BBr3 in CH2Cl2. The mixture was stirred at ambient temperature for 1.5 h, then poured over 60 mL of ice, and extracted with ethyl acetate (2×25 mL). The combined organic layers were back extracted with water (1×25 mL), then brine (1×25 mL), dried over MgSO4, filtered, and concentrated to an oil. This was heated under vacuum at 110° C. to provide the titled compound (308 mg, 94%).

Workup

  1. extractionextracted with ethyl acetate (2×25 mL)
  2. extractionThe combined organic layers were back extracted with water (1×25 mL)
  3. dry with materialbrine (1×25 mL), dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. temperatureThis was heated under vacuum at 110° C.

Sources & evidence

ORD record
ord-4e43ed25b01b4eab98ba1757bb5c222b
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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