Phosphorus tribromide → (2'-Bromomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

HRID 38686Notes

Reaction equation

HRID 38686 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[CH2:24]O)[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2].P(Br)(Br)[Br:28]>COCCOC>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[CH2:24][Br:28])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 67431174(2'-Hydroxymethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

Product 1

HCID 67430388(2'-Bromomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To (2′-hydroxymethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (2.30 mmol) in DME was added phosphorus tribromide (0.26 mL, 2.76 mmol), and the reaction was stirred for 3 hours at room temperature. The mixture was cooled to 0° C., quenched with saturated aqueous NaHCO3, and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography to give the title compound.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customquenched with saturated aqueous NaHCO3
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e673fc95c5dc498dbd7b380bc5559795
Source dataset
uspto-grants-2013_09
Patent number
US08524748B2

Reaction notes

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