Carbon tetrabromide → 3-{4-[3-(3-Allyl-biphenyl-4-yloxy)-propoxy]-phenyl}-2-methoxy-propionic acid ethyl ester

HRID 459176Notes

Reaction equation

HRID 459176 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][CH2:13][OH:14])[CH:2]=[CH2:3].C(Br)(Br)(Br)Br.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2:45]([O:47][C:48](=[O:60])[C@@H:49]([O:58][CH3:59])[CH2:50][C:51]1[CH:56]=[CH:55][C:54](O)=[CH:53][CH:52]=1)[CH3:46]>ClCCl>[CH2:45]([O:47][C:48](=[O:60])[CH:49]([O:58][CH3:59])[CH2:50][C:51]1[CH:56]=[CH:55][C:54]([O:14][CH2:13][CH2:12][CH2:11][O:10][C:9]2[CH:8]=[CH:7][C:6]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:5][C:4]=2[CH2:1][CH:2]=[CH2:3])=[CH:53][CH:52]=1)[CH3:46]

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 11390460(2S)-3-(4-hydroxy-phenyl)-2-methoxypropionic acid ethyl esterHCID 184436063-(3-Allyl-biphenyl-4-yloxy)-propan-1-ol

Product 1

HCID 694229003-{4-[3-(3-Allyl-biphenyl-4-yloxy)-propoxy]-phenyl}-2-methoxy-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound from Step B in dichloromethane was treated with CBr4 (1.12 eq) and PPh3 (1.4 eq) and allow to react for 1.5 hours. The product isolated after chromatography of this reaction was treated under Standard Procedure I with (2S)-3-(4-hydroxy-phenyl)-2-methoxy-propionic acid ethyl ester to give the title compound.

Workup

  1. customto react for 1.5 hours
  2. customThe product isolated after chromatography of this reaction

Sources & evidence

ORD record
ord-cf5cdbbb851f485496c6cb2e8a0b4829
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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