1-Chloro-3-iodobenzene → 5-Bromo-3'-chloro-2-methoxy-biphenyl

HRID 1632095Notes

Reaction equation

HRID 1632095 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6](B(O)O)[CH:7]=1.[Cl:13][C:14]1[CH:15]=[C:16](I)[CH:17]=[CH:18][CH:19]=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:13])[CH:19]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 122691-Chloro-3-iodobenzeneHCID 45327305-Bromo-2-methoxyphenylboronic acid

Product 1

HCID 687911405-Bromo-3'-chloro-2-methoxy-biphenylYield 99%

Procedure

I-208 was synthesized from 5-bromo-2-methoxyphenylboronic acid (2.00 g, 8.66 mmol) and 3-chloroiodobenzene (2.48 g, 10.4 mmol) using the same conditions as for I-207. The reaction time was extended to 16 h. The methanol was removed under vacuum, and the residue dissolved in ethyl acetate (100 mL), washed with water (100 mL), and the aqueous wash extracted with ethyl acetate (100 mL). The combined organic extracts were washed with saturated aqueous sodium bicarbonate (2×200 mL), water (2×200 mL) and brine (150 mL), dried over sodium sulfate, filtered and the solvent removed under vacuum to give I-208 (2.56 g, 99% yield). 1H NMR (400 MHz, CDCl3) 7.49-7.48 (m, 1H), 7.44-7.40 (m, 2H), 7.36-7.31 (m, 3H), 6.85 (d, J=8.4 Hz, 1H), 3.80 (s, 3H) ppm.

Workup

  1. customThe methanol was removed under vacuum
  2. dissolutionthe residue dissolved in ethyl acetate (100 mL)
  3. washwashed with water (100 mL)
  4. washthe aqueous wash
  5. extractionextracted with ethyl acetate (100 mL)
  6. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate (2×200 mL), water (2×200 mL) and brine (150 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent removed under vacuum
  10. customto give I-208 (2.56 g, 99% yield)

Sources & evidence

ORD record
ord-39b69035b32741c48c6ff65252cc51e0
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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