Boron tribromide → HCID 66914765, compound

HRID 880458Notes

Reaction equation

HRID 880458 reaction equation
B(Br)(Br)Br.C[O:6][CH2:7][CH2:8][N:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=[C:10]1[CH3:20]>ClCCl>[CH3:20][C:10]1[N:9]([CH2:8][CH2:7][OH:6])[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66914904HCID 66914904, compound

Product 1

HCID 66914765HCID 66914765, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (0.3 mL, 3.07 mmol) was added drop wise to a solution of 1-(2-methoxyethyl)-2-methyl-4-phenyl-pyrrole (330 mg, 1.53 mmol) in dry dichloromethane (20 mL) at 0 to 5° C. and stirred for 1 h. The reaction mixture was quenched with a 10% sodium bicarbonate solution (20 mL) at 0 to 5° C. and extracted with ethyl acetate (2×25 mL). The organic layer was washed successively with water (2×25 mL), brine (2×25 mL), dried over anhydrous sodium sulphate and concentrated in vacuo to yield 2-(2-methyl-4-phenyl-pyrrol-1-yl)-ethanol (270 mg, 88%) as a brown solid.

Workup

  1. customThe reaction mixture was quenched with a 10% sodium bicarbonate solution (20 mL) at 0 to 5° C.
  2. extractionextracted with ethyl acetate (2×25 mL)
  3. washThe organic layer was washed successively with water (2×25 mL), brine (2×25 mL)
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4c5d4c663aca4ec9b1df29ddeb7700d7
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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