Benzene → 2-Bromobiphenyl

HRID 1591489Notes

Reaction equation

HRID 1591489 reaction equation
C(ON=O)CC(C)C.[Br:9][C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1N.[CH:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[Br:9][C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 241Benzene2×HCID 8053Isoamyl NitriteHCID 119922-Bromoaniline

Product 1

HCID 163292-Bromobiphenyl

Procedure

A solution of 8.8 mL of isoamylnitrite in 120 mL of benzene at 45° C. was treated dropwise over 30 minutes with a solution of 7.5 g of 2-bromoaniline in 30 mL of benzene. After the addition was complete, the mixture was heated at reflux for 90 minutes then cooled and concentrated under vacuum. The product was purified by preparative high presssure liquid chromatography on silica, eluting with hexanes. 1H NMR (200 MHz,CDCl3): 7.23 (m,2H), 7.35 (m,1H), 7.44 (s,5H), 7.70 (d,8 Hz,1H).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 90 minutes
  4. temperaturethen cooled
  5. concentrationconcentrated under vacuum
  6. customThe product was purified by preparative high presssure liquid chromatography on silica
  7. washeluting with hexanes

Sources & evidence

ORD record
ord-4934ab06ec0447f3924722795b5cdba1
Source dataset
uspto-grants-1993_04
Patent number
US05206235

Reaction notes

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