Triphenylphosphine → 4-Bromomethyl-2-(3-chloro-phenoxy)-1-methoxy-benzene

HRID 332576Notes

Reaction equation

HRID 332576 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][C:6]1[CH:7]=[C:8]([CH2:14]O)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C(=O)N([Br:45])C(=O)C1>C(Cl)Cl>[Br:45][CH2:14][C:8]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:6]([O:5][C:4]2[CH:16]=[CH:17][CH:18]=[C:2]([Cl:1])[CH:3]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 57701122[3-(3-Chloro-phenoxy)-4-methoxy-phenyl]-methanol

Product 1

HCID 577011304-Bromomethyl-2-(3-chloro-phenoxy)-1-methoxy-benzeneYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(3-chloro-phenoxy)-4-methoxy-phenyl]-methanol (13) (315 mg, 1.2 mmol) and triphenylphosphine (390 mg, 1.5 mmol) in methylene chloride (5 ml) was added NBS (0.250 mg, 1.4 mmol) in portions at 0° C. under nitrogen. After 10 min of stirring at 0° C., the mixture was allowed to warm to room temperature, and continued to stir for 16 h. After the solvent was removed, the residue was purified by silica gel column chromatography with ether/hexane as eluent to give 360 mg (85% yield) of product (14).

Workup

  1. temperatureto warm to room temperature
  2. stirringto stir for 16 h
  3. customAfter the solvent was removed
  4. customthe residue was purified by silica gel column chromatography with ether/hexane as eluent

Sources & evidence

ORD record
ord-8c044c98209c4847b1ab1c78200d10ff
Source dataset
uspto-grants-2014_11
Patent number
US08877816B2

Reaction notes

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