Boron tribromide → HCID 10450022, compound

HRID 866003Notes

Reaction equation

HRID 866003 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:21]([O-:23])=[O:22])[CH:5]=[C:6]([Cl:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([N+:21]([O-:23])=[O:22])[CH:5]=[C:6]([Cl:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10316208HCID 10316208, compound

Product 1

HCID 10450022HCID 10450022, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3,5-Dichloro-4-(3'-isopropyl-4'-methoxyphenoxy)-nitrobenzene (10.63 g) in 100 ml. dichloromethane is cooled in a dry ice/acetone bath and 60 ml of 1M boron tribromide in dichloromethane is added at less than -40°. After addition is completed, the mixture is stirred 18 hours at room temperature, poured into ice, and extracted twice with ethyl acetate. The combined organic layers are dried, filtered, and stripped to yield 3,5-dichloro-4-(3'-isopropyl-4'-hydroxyphenoxy)-nitrobenzene. NMR(CDCl3): δ1.2 (6H,d), 3.3 (1H,m), 6.5 (1H, d of d), 6.7 (1H,d), 6.8 (1H,d), 8.3 (2H,s).

Workup

  1. additionAfter addition
  2. additionpoured into ice
  3. extractionextracted twice with ethyl acetate
  4. customThe combined organic layers are dried
  5. filtrationfiltered

Sources & evidence

ORD record
ord-d8d1abb7a15e45ed9d1a9c813941b132
Source dataset
uspto-grants-1996_10
Patent number
US05569674

Reaction notes

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