Boron tribromide → HCID 89480432, compound

HRID 589254Notes

Reaction equation

HRID 589254 reaction equation
[F:1][C:2]1([F:53])[C:6]([F:8])([F:7])[C:5]([F:10])([F:9])[C:4]([C:11]2[C:15]3[CH:16]=[CH:17][C:18]([O:20]C)=[CH:19][C:14]=3[O:13][C:12]=2[C:22]2[CH:27]=[CH:26][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:24][CH:23]=2)=[C:3]1[C:32]1[C:36]2[CH:37]=[CH:38][C:39]([O:41]C)=[CH:40][C:35]=2[O:34][C:33]=1[C:43]1[CH:48]=[CH:47][C:46]([C:49]([CH3:52])([CH3:51])[CH3:50])=[CH:45][CH:44]=1.BrB(Br)Br>ClCCl>[F:10][C:5]1([F:9])[C:6]([F:8])([F:7])[C:2]([F:1])([F:53])[C:3]([C:32]2[C:36]3[CH:37]=[CH:38][C:39]([OH:41])=[CH:40][C:35]=3[O:34][C:33]=2[C:43]2[CH:44]=[CH:45][C:46]([C:49]([CH3:52])([CH3:51])[CH3:50])=[CH:47][CH:48]=2)=[C:4]1[C:11]1[C:15]2[CH:16]=[CH:17][C:18]([OH:20])=[CH:19][C:14]=2[O:13][C:12]=1[C:22]1[CH:23]=[CH:24][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 89480475HCID 89480475, compound

Product 1

HCID 89480432HCID 89480432, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a one neck round bottom flask containing a solution of 3,3′-(perfluorocyclopent-1-ene-1,2-diyl)bis(2-(4-(tert-butyl)phenyl)-6-methoxybenzofuran) (1 g, 1.365 mmol) in anhydrous dichloromethane (Ratio: 1, Volume: 50 ml) at room temperature was added dropwise tribromoborane (1.8 ml, 18.68 mmol). The reaction mixture was stirred at reflux for 2 hours. The TLC after 2 hours showed that all the starting material was consumed. The reaction was quenched with methanol (vigorous reaction). The crude was washed with an aqueous solution of 10% HCl, extracted with DCM, then dried over anhydrous magnesium sulfate. The solid obtained was deposited on silica gel and purified by chromatography column using CombiFlash Rf eluting with pure DCM to obtain the product 3,3′-(perfluorocyclopent-1-ene-1,2-diyl)bis(2-(4-(tert-butyl)phenyl)benzofuran-6-ol) (0.96 g, 1.362 mmol, 100% yield) as fluffy yellow solid. 1H NMR (500 MHz, CDCl3) δ 7.1 (AB, J=8.4 Hz, 8H), 7.06 (m, 2H), 6.73 (d, J=2.1 Hz, 2H), 6.54 (dd, J=8.6, 2.2 Hz, 2H), 4.77 (s, 2H), 1.18 (s, 18H).

Workup

  1. temperatureat reflux for 2 hours
  2. customthe starting material was consumed
  3. customThe reaction was quenched with methanol (vigorous reaction)
  4. washThe crude was washed with an aqueous solution of 10% HCl
  5. extractionextracted with DCM
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solid obtained
  8. custompurified by chromatography column
  9. washeluting with pure DCM

Sources & evidence

ORD record
ord-d51cd2d7d5d24784ad21f73f632106fe
Source dataset
uspto-grants-2016_01
Patent number
US09227986B2

Reaction notes

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