Triphenylphosphine → 3-Bromomethyl-3'-chloro-2-fluoro-6-methoxy-biphenyl

HRID 1632028Notes

Reaction equation

HRID 1632028 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH2:16]O)[C:9]=2[F:18])[CH:5]=[CH:6][CH:7]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C(=O)N([Br:45])C(=O)C1>ClCCl>[Br:45][CH2:16][C:10]1[C:9]([F:18])=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:13]([O:14][CH3:15])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 57703788(3'-Chloro-2-fluoro-6-methoxy-biphenyl-3-yl)-methanol

Product 1

HCID 577037013-Bromomethyl-3'-chloro-2-fluoro-6-methoxy-biphenylYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a 250 mL round bottom flask was added (3′-Chloro-2-fluoro-6-methoxy-biphenyl-3-yl)-methanol synthesized above (1.21 g, 4.54 mmol), dichloromethane (20 mL), PPh3 (1.19 g, 4.54 mmol), and the solution was cooled to 0° C. NBS (0.81 g, 4.54 mmol) was added and the reaction stirred for 2 hours at 0° C. The organics were washed with H2O and concentrated. The residue was purified by flash column chromatography eluting with 8% ethyl acetate/hexanes to give 3-bromomethyl-3′-chloro-2-fluoro-6-methoxy-biphenyl (I-33, 956 mg, 64%) as an off-white solid.

Workup

  1. washThe organics were washed with H2O
  2. concentrationconcentrated
  3. customThe residue was purified by flash column chromatography
  4. washeluting with 8% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-a727f74f25394562bc20bb60fa691d40
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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