HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Boron trifluoride etherate → 2-(5-Bromo-2-chlorobenzyl)-1-benzothiophene

HRID 604712
Notes
Print preview

Reaction equation

HRID 604712 reaction equation
[SiH](CC)(CC)CC.B(F)(F)F.CCOCC.[S:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH:19]=[C:18]1[CH:26]([C:28]1[CH:33]=[C:32]([Br:34])[CH:31]=[CH:30][C:29]=1[Cl:35])O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Br:34][C:32]1[CH:31]=[CH:30][C:29]([Cl:35])=[C:28]([CH:33]=1)[CH2:26][C:18]1[S:17][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 231033831-Benzothien-2-yl(5-bromo-2-chlorophenyl)methanol

Product 1

HCID 581784582-(5-Bromo-2-chlorobenzyl)-1-benzothiopheneYield 56.6%

Reagents, catalysts & solvents 1

HCID 6212
Chloroform
Solvent

Procedure

Then, Et3SiH (9.2 mL, 0.058 mol) and BF3.Et2O (3.6 mL, 0.029 mol) were added sequentially to a chloroform (110 mL) solution of (1-benzothien-2-yl)(5-bromo-2-chlorophenyl)methanol (10.2 g, 0.0288 mol) at −15° C. The reaction mixture was warmed to room temperature and stirred at the temperature for ten hours. After the reaction mixture was added with a saturated sodium bicarbonate aqueous solution, the organic phase was separated, washed with brine and then dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=60:1) to obtain a colorless oily title compound (5.5 g, 56%).

Workup

  1. customthe organic phase was separated
  2. washwashed with brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationAfter the desiccant was filtered off
  5. customthe residue obtained
  6. customby evaporating the solvent under reduced pressure
  7. customwas purified by silica gel column chromatography (hexane:ethyl acetate=60:1)

Sources & evidence

ORD record
ord-f575734f517d4f549509e9638ed86b05
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07910619B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes