Boron tribromide → 4-(2,6-Dibromo-4-nitrophenoxy)-2-isopropylphenol

HRID 2108669Notes

Reaction equation

HRID 2108669 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:21]([O-:23])=[O:22])[CH:5]=[C:6]([Br: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>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([N+:21]([O-:23])=[O:22])[CH:5]=[C:6]([Br: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 117442094-(2,6-Dibromo-4-nitrophenoxy)-2-isopropylanisole

Product 1

HCID 226603024-(2,6-Dibromo-4-nitrophenoxy)-2-isopropylphenolYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3,5-dibromo-4-(3′-isopropyl-4′-methoxyphenoxy)-nitrobenzene (1.37 g, 2.98 mmol) in CH2Cl2 (30.0 mL) at −78° C. was added BBr3 (8.93 mL, 8.93 mmol, 1 M solution in CH2Cl2). The reaction mixture was stirred at room temperature for 2.5 h, quenched with ice/water, and stirred cold for several minutes. The reaction mixture was diluted with CH2Cl2 and H2O, partitioned, and the aqueous solution was extracted with CH2Cl2. The combined organic layers were concentrated under reduced pressure and the residue was purified by column chromatography on silica gel, eluting with ethyl acetate-hexanes (1:10) to afford 3,5-dibromo-4-(4′-hydroxy-3′-isopropylphenoxy)nitrobenzene as a solid (1.20 g, 90%): 1H NMR (300 MHz, DMSO-d6): δ 9.19 (s, 1H), 8.64 (s, 2H), 6.73 (m, 2H), 6.37 (m, 1H), 3.12 (m, 1H), 1.16 (d, J=6.0 Hz, 6H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (1:5); Rf=0.46.

Workup

  1. customquenched with ice/water
  2. stirringstirred cold for several minutes
  3. additionThe reaction mixture was diluted with CH2Cl2 and H2O
  4. custompartitioned
  5. extractionthe aqueous solution was extracted with CH2Cl2
  6. concentrationThe combined organic layers were concentrated under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel
  8. washeluting with ethyl acetate-hexanes (1:10)

Sources & evidence

ORD record
ord-4857a9ff8c2b42029ba7a4a99970ded9
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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