Hexane → 1-Benzothien-7-ylboronic acid

HRID 2117334Notes

Reaction equation

HRID 2117334 reaction equation
Br[C:2]1[C:10]2[S:9][CH:8]=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.[B:22](OC)([O:25]C)[O:23]C>CCOCC>[S:9]1[C:10]2[C:2]([B:22]([OH:25])[OH:23])=[CH:3][CH:4]=[CH:5][C:6]=2[CH:7]=[CH:8]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8470Trimethyl borateHCID 120455387-Bromobenzo[b]thiopheneHCID 178418339Butyllithium

Product 1

HCID 166405281-Benzothien-7-ylboronic acidYield 60%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of 7-bromo-1-benzothiophene (19.9 g, 0.094 mol) in absolute ether (200 ml) was treated with a 1.6 M solution of n-butyllithium in hexane (0.14 mol, 88 ml) at −78° C. The solution was stiffed at −78° C. for 10 minutes then treated with trimethyl borate (15 ml, 0.14 mol). The mixture was allowed to warm to −10° C. then quenched with an excess of dilute hydrochloric acid. The organic layer was separated, dried, evaporated, and the residue was recrystallised from aqueous ethanol to yield the title compound (10 g, 60%).

Workup

  1. customthen quenched with an excess of dilute hydrochloric acid
  2. customThe organic layer was separated
  3. customdried
  4. customevaporated
  5. customthe residue was recrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-ece564e6cbef422489e0a200676991f5
Source dataset
uspto-grants-2008_10
Patent number
US07442701B2

Reaction notes

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