Boron tribromide → HCID 66642897, compound

HRID 2108610Notes

Reaction equation

HRID 2108610 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:27])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17]C)=[C:13]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH:12]=1)[CH2:5]O.B(Br)(Br)[Br:29]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:27])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH:12]=1)[CH2:5][Br:29]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66642809HCID 66642809, compound

Product 1

HCID 66642897HCID 66642897, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3,5-dichloro-4-[3′-(4-fluorobenzyl)-4′-methoxyphenoxy] benzyl alcohol (0.53 g, 1.29 mmol) in CH2Cl2 (20 mL) at −78° C. was added BBr3 (0.82 g, 3.2 mmol). The reaction mixture was stirred at room temperature for 16 h, poured into ice water (100 mL) and extracted with CH2Cl2 (200 mL). The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluted with ethyl acetate-hexanes (1:4) to afford 3,5-dichloro-4-[3′-(4-fluorobenzyl)-4′-hydroxyphenoxy] benzyl bromide as a colorless oil (0.4 g, 67%): 1H NMR (300 MHz, CDCl3): δ 7.39 (s, 2H), 7.14 (dd, J=5.4, 8.7 Hz, 2H), 6.95 (t, J=8.7 Hz, 2H), 6.66 (d, J=9.0 Hz, 1H), 6.62 (d, J=2.7 Hz, 1H), 6.53 (dd, J=3.0, 8.7 Hz, 1H), 4.04 (s, 2H), 3.90 (s, 2H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (1:4); Rf=0.8.

Workup

  1. extractionextracted with CH2Cl2 (200 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel
  7. washeluted with ethyl acetate-hexanes (1:4)

Sources & evidence

ORD record
ord-175829c3f64e4bd5ace2c21f707a4a97
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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