Phosphorus tribromide → HCID 66707504, compound

HRID 1496934Notes

Reaction equation

HRID 1496934 reaction equation
P(Br)(Br)[Br:2].[F:5][C:6]([F:25])([F:24])[O:7][C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][C:19]([CH2:22]O)=[CH:18][CH:17]=2)=[CH:10][CH:9]=1>C(Cl)Cl>[Br:2][CH2:22][C:19]1[CH:20]=[CH:21][C:16](/[CH:15]=[CH:14]/[C:11]2[CH:12]=[CH:13][C:8]([O:7][C:6]([F:25])([F:24])[F:5])=[CH:9][CH:10]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 66707167HCID 66707167, compound

Product 1

HCID 66707504HCID 66707504, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PBr3 (56 μL, 0.60 mmol) was added to a solution of alcohol 127 (0.177 g, 0.601 mmol) in anhydrous CH2Cl2 (10 mL) at 0° C. The mixture was stirred at room temperature for 1 h, and then cooled to 0° C., quenched with ice, and extracted with CH2Cl2. The organic fraction was dried, and evaporated, and then column chromatography of the residue, eluting with CH2Cl2, gave 1-{(E)-2-[4-(bromomethyl)phenyl]ethenyl}-4-(trifluoromethoxy)benzene (128) (0.125 g, 58%) as a white solid: mp 100-102° C.; 1H NMR (CDCl3) δ 7.52 (d, J=8.6 Hz, 2H), 7.48 (d, J=8.3 Hz, 2H), 7.39 (d, J=8.3 Hz, 2H), 7.20 (br d, J=8.1 Hz, 2H), 7.10 (d, J=16.3 Hz, 1H), 7.05 (d, J=16.3 Hz, 1H), 4.51 (s, 2H). APCI MS m/z 277 [M+H−HBr]+.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched with ice
  3. extractionextracted with CH2Cl2
  4. customThe organic fraction was dried
  5. customevaporated
  6. washcolumn chromatography of the residue, eluting with CH2Cl2

Sources & evidence

ORD record
ord-72ab1dd2dbdc49acbbf484f18f1eef6f
Source dataset
uspto-grants-2015_12
Patent number
US09198913B2

Reaction notes

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