Boron tribromide → HCID 18690200, compound

HRID 616644Notes

Reaction equation

HRID 616644 reaction equation
C[O:2][C:3]1[CH:27]=[CH:26][C:6]([C:7]([C:9]2[CH2:10][C:11]3[C:16]([C:17]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:15][CH:14]=[C:13]([O:24]C)[CH:12]=3)=[O:8])=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:27]=[CH:26][C:6]([C:7]([C:9]2[CH2:10][C:11]3[C:16]([C:17]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:15][CH:14]=[C:13]([OH:24])[CH:12]=3)=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 18690169HCID 18690169, compound

Product 1

HCID 18690200HCID 18690200, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4 gms. of the product from Example 1 in dichloromethane were added two equivalents of boron tribromide. The resulting mixture was stirred for 24 hours. Analysis of the reaction mixture by TLC indicated the presence of starting material, product, and some of the monohydroxy compound. Another equivalent of boron tribromide was added, and the mixture was stirred for a total of 72 hrs. TLC indicated no starting material and only traces of the monohydroxy derivative. The product was chromatographed on silica using a mixture of 10 percent ethyl acetate and 90 percent benzene to obtain 3 gms. of the title compound, m.p. 191°-192° C.

Workup

  1. stirringthe mixture was stirred for a total of 72 hrs
  2. customThe product was chromatographed on silica using
  3. additiona mixture of 10 percent ethyl acetate and 90 percent benzene
  4. customto obtain 3 gms

Sources & evidence

ORD record
ord-9b576e895b6f41b18518fcb43857ec82
Source dataset
uspto-grants-1978_02
Patent number
US04075223

Reaction notes

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