Dichloromethane → HCID 68534083, compound

HRID 2108668Notes

Reaction equation

HRID 2108668 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:26])[CH:5]=[C:6]([Br:25])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:10]=1.ClCCl.B(Br)(Br)Br>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([OH:26])[CH:5]=[C:6]([Br:25])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 68531060HCID 68531060, compound

Product 1

HCID 68534083HCID 68534083, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3,5-dibromo-4-[3′-(4-fluorobenzyl)-4′-methoxyphenoxy]phenol (1.66 gm, 3.44 mmol), dichloromethane 100 mL, was added boron tribromide (8.6 mL, 8.60 mmol) in an ice/water bath. The reaction was stirred overnight under a nitrogen atmosphere. The reaction was diluted with ethyl acetate 60 mL, filtered and washed with water 2× with 10 mL and brine 3×10 mL. The ethyl acetate was dried over Na2SO4, filtered and concentrated under reduced pressure. 3,5-Dibromo-4-[3′-(4-fluorobenzyl)-4′-hydroxyphenoxy]phenol (1.06 gm, 66%) was obtained by flash chromatography using SiO2 eluted with a step gradient of hexane-ethyl acetate[3:1] 2L and hexane-ethyl acetate [3:2]; 1H NMR (300 MHz, DMSO-d6): δ 10.24 (s, 1H), 9.14 (s, 1H), 7.22 (m, 2H), 7.08 (m, 4H), 6.69 (td, J=8.7 Hz, 1H), 6.54 (d, J=3.3 Hz, 1H), 6.55 (dd, J=8.4, 3.3 Hz, 1H), 6.35 (dd, J=9, 3 Hz, 1H), 3.80 (s, 2H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=methylene chloride-hexanes (1:1); Rf=0.55.

Workup

  1. filtrationfiltered
  2. washwashed with water 2× with 10 mL and brine 3×10 mL
  3. dry with materialThe ethyl acetate was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ca294373bf74da1bc178abe7c6f3777
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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