Dichloromethane → 6,6′-Diiodo[1,1′-biphenyl]-3,3′-diol

HRID 2119238Notes

Reaction equation

HRID 2119238 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]([I:18])=[C:7]([C:9]2[CH:14]=[C:13]([O:15]C)[CH:12]=[CH:11][C:10]=2[I:17])[CH:8]=1.B(Br)(Br)Br.C(Cl)Cl>C(=O)=O.CC(C)=O>[OH:15][C:13]1[CH:12]=[CH:11][C:10]([I:17])=[C:9]([C:7]2[CH:8]=[C:3]([OH:2])[CH:4]=[CH:5][C:6]=2[I:18])[CH:14]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 10895916HCID 10895916, compound

Product 1

HCID 226253006,6′-Diiodo[1,1′-biphenyl]-3,3′-diolYield 85%

Reagents, catalysts & solvents 1

HCID 18522661Acetone cardiceSolvent

Procedure

A flask containing 5,5'-dimethoxy-2,2'-diiodobiphenyl (10.0 g, 21 mmol) was cooled to -76° C. in dry ice/acetone. A 1.0M solution of boron tribromide in methylene chloride (64 ml, 64 mmol) was added via syringe to the cold substrate. The ice bath was removed and the reaction allowed to reach room temperature. After 18 hours, the solution was added slowly to 1 L of water. The aqueous mixture was stirred for 2 hours, and the white solid which formed was filtered, washed with water, and dried to give I, which melted at 181°-182° C., in 85% yield.

Workup

  1. customThe ice bath was removed
  2. customto reach room temperature
  3. additionthe solution was added slowly to 1 L of water
  4. customthe white solid which formed
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried
  8. customto give I, which melted at 181°-182° C.

Sources & evidence

ORD record
ord-07a05e9b195d48fb839d4f62d4dc8d3f
Source dataset
uspto-grants-1987_07
Patent number
US04683340

Reaction notes

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