1-Bromo-3-chloropropane → 5-Octyl-2-[4-(3-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy)phenyl]pyrimidine

HRID 582973Notes

Reaction equation

HRID 582973 reaction equation
[F:1][C:2]([F:28])([F:27])[O:3][C:4]([F:26])([F:25])[C:5]([F:24])([F:23])[O:6][C:7]([F:22])([F:21])[C:8]([F:20])([F:19])[O:9][C:10]([F:18])([F:17])[CH2:11][O:12][CH2:13][CH2:14][CH2:15]Cl.BrCCCCl.FC(F)(F)OC(F)(F)C(F)(F)OC(F)(F)C(F)(F)OC(F)(F)CO.[CH2:58]([C:66]1[CH:67]=[N:68][C:69]([C:72]2[CH:77]=[CH:76][C:75]([OH:78])=[CH:74][CH:73]=2)=[N:70][CH:71]=1)[CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65]>>[CH2:58]([C:66]1[CH:71]=[N:70][C:69]([C:72]2[CH:77]=[CH:76][C:75]([O:78][CH2:15][CH2:14][CH2:13][O:12][CH2:11][C:10]([O:9][C:8]([F:19])([F:20])[C:7]([F:21])([F:22])[O:6][C:5]([F:23])([F:24])[C:4]([F:25])([F:26])[O:3][C:2]([F:28])([F:27])[F:1])([F:18])[F:17])=[CH:74][CH:73]=2)=[N:68][CH:67]=1)[CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65]

Participants

5

Reactant 4

HCID 80061-Bromo-3-chloropropaneHCID 6040552-(4-Hydroxyphenyl)-5-octylpyrimidineHCID 27781611H,1H-Tridecafluoro-3,6,9-trioxadecan-1-olHCID 212252903-(2-(2-(2-(Trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propyl chloride

Product 1

HCID 212253045-Octyl-2-[4-(3-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy)phenyl]pyrimidine

Procedure

The title compound was prepared essentially as in Example 1 by combining 3-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)1-chloropropane (18.3 g, 38.5 mmol; prepared from 1-bromo-3-chloropropane (107 g, 0.7 mol) and 2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethanol (125 g, 0.31 mol) essentially as in Example 2) with 5-octyl-2-(4-hydroxyphenyl)pyrimidine (10 g, 35 mmol). The crude product was further purified by Kugelrohr distillation (b.p. 200-210° C. at 0.4 torr; yield of 10.0 g).

Workup

  1. distillationThe crude product was further purified by Kugelrohr distillation (b.p. 200-210° C. at 0.4 torr; yield of 10.0 g)

Sources & evidence

ORD record
ord-ff2cb90eec324317b7d23686689981af
Source dataset
uspto-grants-1999_07
Patent number
US05928562

Reaction notes

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