1-Bromo-4-(pentafluoro-lambda6-sulfanyl)benzene → HCID 86591924, compound

HRID 2214331Notes

Reaction equation

HRID 2214331 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([F:13])([F:12])([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[F:14][C:15]1[CH:20]=[C:19]([CH2:21][C@H:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH3:23])[CH:18]=[C:17]([F:30])[C:16]=1OB(O)O.C1([C@H](C)CC2C=CC(OB(O)O)=CC=2)C=CC=CC=1>>[F:14][C:15]1[CH:20]=[C:19]([CH2:21][C@H:22]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH3:23])[CH:18]=[C:17]([F:30])[C:16]=1[C:2]1[CH:7]=[CH:6][C:5]([S:8]([F:13])([F:12])([F:11])([F:10])[F:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 27791941-Bromo-4-(pentafluoro-lambda6-sulfanyl)benzeneHCID 21052392HCID 21052392, compoundHCID 21052393HCID 21052393, compound

Product 1

HCID 86591924HCID 86591924, compoundYield 43%

Procedure

A reaction was carried out in the same manner as in second step of Example 4-3 except that 3.08 g (10.9 mmol) of 4-bromophenyl sulfur pentafluoride [Br-Ph-SF5] was employed instead of 1-bromo-3,5-difluorobenzene in second step of Example 4-3 and 3.00 g (10.9 mmol) of (R)-2,6-difluoro-4-(2-phenylpropyl)phenylboric acid [H-Ph-CH(CH3)—CH2-PhFF-B(OH)2] obtained in third step of Example 4-5 was employed instead of (R)-4-(2-phenylpropyl)phenylboric acid [H-Ph-CH(CH3)—CH2-Ph-B(OH)2] to obtain 2.03 g (4.67 mmol) of (R)-4-(2,6-difluoro-4-(2-phenylpropyl)phenyl)phenyl sulfur pentafluoride [H-Ph-CH(CH3)—CH2-PhFF-Ph-SF5] (yield: 43%). MS m/e: 434(M+)

Workup

  1. customobtained in third step of Example 4-5

Sources & evidence

ORD record
ord-c17ab3449e1b4f40a26271c2ee3baa70
Source dataset
uspto-grants-2006_09
Patent number
US07108895B2

Reaction notes

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