HCID 10524046, compound → HCID 10580124, compound

HRID 1977917Notes

Reaction equation

HRID 1977917 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[C:12]=2[CH2:18][CH2:19][CH3:20])=[CH:8][CH:7]=[CH:6][C:5]=1[F:21].[CH2:23]([O:30][C:31]1[CH:36]=[C:35]([O:37][CH2:38][CH2:39][CH2:40]Cl)[C:34]([CH2:42][CH3:43])=[CH:33][C:32]=1[Br:44])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:40][CH2:39][CH2:38][O:37][C:35]3[CH:36]=[C:31]([O:30][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:32]([Br:44])=[CH:33][C:34]=3[CH2:42][CH3:43])[C:12]=2[CH2:18][CH2:19][CH3:20])=[CH:8][CH:7]=[CH:6][C:5]=1[F:21]

Participants

3

Reactant 2

HCID 10524046HCID 10524046, compoundHCID 10733286HCID 10733286, compound

Product 1

HCID 10580124HCID 10580124, compound

Procedure

2-Fluoro-6-(3-hydroxy-2-propylphenoxy)benzoic acid methyl ester (1.84 g, 4.80 mmol) was alkylated with 2-benzyloxy-1-bromo-5-ethyl-4-(3-chloro-1-propyloxy)benzene to provide crude product as an oil. Silica gel chromatography provided 2.05 g (66%) of the purified title intermediate as a colorless oil: NMR (CDCl3) 7.49 (d, J=7.1 Hz, 2H), 7.20-7.45 (m, 5H), 7.14 (t, J=8.2 Hz, 1H), 6.82 (t, J=8.5 Hz, 1H), 6.73 (d, J=8.3 Hz, 1H), 6.60 (d, J=8.4 Hz, 1H), 6.53 (s, 1H), 6.52 (d, J=8.5 Hz, 1H), 5.13 (s, 2H), 4.20 (t, J=6.0 Hz, 2H), 4.13 (t, J=6.0 Hz, 2H), 3.92 (s, 3H), 2.58 (m, 4H), 2.30 (quintet, J=6.0 Hz, 2H), 1.51 (hextet, J=7.6 Hz, 2H), 1.16 (t, J=7.9 Hz, 3H), 0.90 (t, J=7.3 Hz, 3H).

Workup

  1. customto provide crude product as an oil
  2. customSilica gel chromatography provided 2.05 g (66%) of the
  3. custompurified title intermediate as a colorless oil

Sources & evidence

ORD record
ord-284eff20416c4fcf823d8269cb586cef
Source dataset
uspto-grants-2001_05
Patent number
US06235785B1

Reaction notes

Loading…