Phosphorus tribromide → 2-[4-(4-Bromomethylphenoxy)-phenyl]-3-(3,5-dimethoxyphenyl)-acrylic acid methyl ester

HRID 2238246Notes

Reaction equation

HRID 2238246 reaction equation
P(Br)(Br)[Br:2].[CH3:5][O:6][C:7](=[O:35])[C:8]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33]O)=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)=[CH:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([O:18][CH3:19])[CH:11]=1>C(Cl)Cl>[CH3:5][O:6][C:7](=[O:35])[C:8]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33][Br:2])=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)=[CH:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([O:18][CH3:19])[CH:11]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 68790209HCID 68790209, compound

Product 1

HCID 687897972-[4-(4-Bromomethylphenoxy)-phenyl]-3-(3,5-dimethoxyphenyl)-acrylic acid methyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of PBr3 (4.8 mL of 1.0 M in CH2Cl2) was added dropwise to 12 (5.0 g, 11.9 mmol) dissolved in CH2Cl2 (20 mL) at temperature with good stirring. After 1 h, the solution was extracted with water (2×60 mL) and brine (20 mL). The organic phase was dried over anhydrous magnesium sulfate, filtered through a small bed of silica gel (20 g) and solvent was evaporated. The resulting tacky syrup was dried under high vacuum for 48 h at room temperature to yield the title compound (5.7 g, 99%): mp 79-81° C.; 1H NMR (400 MHz, DMSO-d6) δ 7.73 (s, 1H), 7.49 (d, J=8.4 Hz, 2H), 7.22 (d, J=8.4 Hz, 2H), 7.07 (d, J=8.4 Hz, 2H), 7.00 (d, J=8.4 Hz, 2H), 6.42 (t, J=2.4 Hz, 1H), 6.28 (d, J=2.0 Hz, 2H), 4.73 (d, J=4.8 Hz, 2H), 3.68 (s, 3H), 3.58 (s, 6H); Anal. (C25H23BrO5) C: calculated, 61.12; found, 62.26; H: calculated 4.80; found 4.88.

Workup

  1. extractionthe solution was extracted with water (2×60 mL) and brine (20 mL)
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. filtrationfiltered through a small bed of silica gel (20 g) and solvent
  4. customwas evaporated
  5. customThe resulting tacky syrup was dried under high vacuum for 48 h at room temperature

Sources & evidence

ORD record
ord-36c642d0f5fb49039789c402f2fb09a0
Source dataset
uspto-grants-2010_05
Patent number
US07718682B2

Reaction notes

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