Phosphorus tribromide → 4-[(1E)-3-bromo-1-propenyl]-4'-(trifluoromethoxy)-1,1'-biphenyl

HRID 1496922Notes

Reaction equation

HRID 1496922 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]([C:14]2[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[CH2:22]O)=[CH:16][CH:15]=2)=[CH:10][CH:9]=1>CCOCC>[Br:2][CH2:22]/[CH:21]=[CH:20]/[C:17]1[CH:18]=[CH:19][C: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:15][CH:16]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 54756895HCID 54756895, compound

Product 1

HCID 547573004-[(1E)-3-bromo-1-propenyl]-4'-(trifluoromethoxy)-1,1'-biphenylYield 123%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

PBr3 (26 μL, 0.28 mmol) was added to a solution of alcohol 101 (0.159 g, 0.540 mmol) in Et2O (10 mL) at 0° C. The mixture was warmed to room temperature and stirred for 1 h, then quenched with ice and extracted with Et2O. The organic fraction was dried and evaporated, and then column chromatography of the residue on silica gel (eluting with CH2Cl2) gave 4-[(1E)-3-bromo-1-propenyl]-4′-(trifluoromethoxy)-1,1′-biphenyl (102) (0.123 g, 71%) as a white solid: mp 121-123° C.; 1H NMR (CDCl3) δ 7.60 (d, J=8.8 Hz, 2H), 7.53 (d, J=8.4 Hz, 2H), 7.46 (d, J=8.4 Hz, 2H), 7.28 (d, J=8.8 Hz, 2H), 6.69 (d, J=15.6 Hz, 1H), 6.45 (dt, J=15.6, 7.8 Hz, 1H), 4.18 (dd, J=7.8, 0.9 Hz, 2H). APCI MS m/z 277 [M+H−HBr]+.

Workup

  1. customquenched with ice
  2. extractionextracted with Et2O
  3. customThe organic fraction was dried
  4. customevaporated

Sources & evidence

ORD record
ord-a3aa2659d02042039112e9fcc548a544
Source dataset
uspto-grants-2015_12
Patent number
US09198913B2

Reaction notes

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