Hydrochloric Acid → HCID 22508333, compound

HRID 984757Notes

Reaction equation

HRID 984757 reaction equation
[CH2:1]([C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15](Br)=[CH:14][C:12]=2[CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C([Li])CCC.C[O:25][B:26](OC)[O:27]C.Cl>CCCCCC.O1CCCC1>[CH2:1]([C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([B:26]([OH:27])[OH:25])=[CH:14][C:12]=2[CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 22508331HCID 22508331, compoundHCID 178418339Butyllithium

Product 1

HCID 22508333HCID 22508333, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

In a 500 ml-three-necked flask, 19.0 g (61.5 mM) of 2-octyl-5-bromobenzofuran (II) and 190 ml of anhydrous tetrahydrofuran (THF) were placed. To the mixture, 45 ml (72.0 mM) of 1.6M-n-butyllithium solution in hexane was added dropwise under argon stream at −70° C. or below in 30 min., followed by stirring at that temperature for 4 hours. To the resultant mixture, a solution of 17.8 g (171 mM) of trimethylborate in 70 ml of anhydrous THF was added dropwise at −70° C. or below in 20 min., and stirred at that temperature for 2 hours. The system was heated up to room temperature and stirred for 17 hours. To the reaction mixture, 100 ml of 10%-hydrochloric acid was added dropwise, followed by extraction with ether. The organic layer was washed with water and dried with anhydrous sodium sulfate, followed by distilling-off of the solvent under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) to obtain a white crystal of 2-octylbenzofuran-5-boronic acid (III) (Yield: 10.8 g (64.1%)).

Workup

  1. stirringstirred at that temperature for 2 hours
  2. stirringstirred for 17 hours
  3. extractionfollowed by extraction with ether
  4. washThe organic layer was washed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customto obtain a residue
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-e77cbe3a4f8849d0a71656aed9944190
Source dataset
uspto-grants-2005_03
Patent number
US06869694B2

Reaction notes

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