Triphenylphosphine → HCID 67324702, compound

HRID 1028981

Reaction equation

HRID 1028981 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][OH:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][C:32]=1O.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][O:10][C:32]1[CH:33]=[C:34]([C:37]([F:39])([F:40])[F:38])[CH:35]=[CH:36][C:31]=1[Cl:30]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 123498Phenol, 2-chloro-5-(trifluoromethyl)-HCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 52987706(2-Bromo-3-methylphenyl)methanol

Product 1

HCID 67324702HCID 67324702, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-bromo-3-methylphenyl)methanol (0.5 g, 2.49 mmol), triphenylphosphine (1.31 g, 4.97 mmol) and 2-chloro-5-(trifluoromethyl)phenol (0.37 mL, 2.74 mmol) in DCM (12.4 mL) at 0° C. was added diethyl azodicarboxylate (1.97 mL, 4.97 mmol) and the reaction warmed to RT for 30 min. The reaction was quenched with water and the aqueous layer was extracted with EtOAc. The organic layer was then washed with water and brine (3× ea.), dried over Na2SO4 and concentrated in vacuo. The crude material was purified by column chromatography (0-50% Hexene/EtOAc) to afford 2-bromo-1-((2-chloro-5-(trifluoromethyl)phenoxy)methyl)-3-methylbenzene as a clear oil.

Workup

  1. customThe reaction was quenched with water
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe organic layer was then washed with water and brine (3× ea.)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by column chromatography (0-50% Hexene/EtOAc)

Sources & evidence

ORD record
ord-e3f1a608aece4bdfb61e9b6616cbd648
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Linked notes

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