Boron tribromide → (4-Hydroxyphenyl)(4-iodophenyl)methanone

HRID 750063Notes

Reaction equation

HRID 750063 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22132674(4-Iodophenyl)(4-methoxyphenyl)methanone

Product 1

HCID 13453359(4-Hydroxyphenyl)(4-iodophenyl)methanoneYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-iodo-phenyl)-(4-methoxy-phenyl)-methanone (1.7 g, 5 mmol in CH2Cl2 (20 mL) was added BBr3 (15 mL, 15 mmol; 1 M in CH2Cl2) at −78° C. The resulting mixture was allowed to warm to rt and stir at rt for 6 h. The mixture was poured onto 50 mL ice-water solution and extracted with CH2Cl2 (3×30 mL). The combined organic layers were washed with water (2×30 mL) and brine (20 mL) and dried over anhy. Na2SO4. The solvent was removed in vacuo to obtain the crude product which was purified by recrystallization from acetone-EtOAc-hexane to provide the title product (1.4 g, 85%) which was directly used for the next step.

Workup

  1. extractionextracted with CH2Cl2 (3×30 mL)
  2. washThe combined organic layers were washed with water (2×30 mL) and brine (20 mL)
  3. customdried over anhy
  4. customThe solvent was removed in vacuo
  5. customto obtain the crude product which
  6. customwas purified by recrystallization from acetone-EtOAc-hexane

Sources & evidence

ORD record
ord-101348b15a884422a9340f917ddf524b
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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