Boron tribromide → HCID 11085183, compound

HRID 1862000Notes

Reaction equation

HRID 1862000 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10966276HCID 10966276, compound

Product 1

HCID 11085183HCID 11085183, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

2-(3-Methoxyphenyl)nitrobenzene, as described above in Step A, (8.6 g, 37.52 mmol) was dissolved in CH2Cl2 (500 mL) and cooled to −78° C. BBr3 (1.0M sol. in CH2Cl2, 43 mL, 43 mmol) was slowly added and the reaction was warmed to ambient temperature and stirred for 18 hours. The reaction was partitioned between saturated aqueous NaHCO3 and CH2Cl2 and extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo, to yield the above-titled compound.

Workup

  1. temperaturethe reaction was warmed to ambient temperature
  2. customThe reaction was partitioned between saturated aqueous NaHCO3 and CH2Cl2
  3. extractionextracted with CH2Cl2 (3×)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7b90821b4b5e47ab8481eb04533af2ae
Source dataset
uspto-grants-2003_03
Patent number
US06534506B2

Reaction notes

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