Boron tribromide → HCID 22241506, compound

HRID 892206Notes

Reaction equation

HRID 892206 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([S:13][CH2:14][C:15]2[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:16]=2[C:17]([O:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[O:18])[CH:10]=[CH:11][CH:12]=1>ClCCl>[OH:6][C:7]1[CH:8]=[C:9]([S:13][CH2:14][C:15]2[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:16]=2[C:17]([O:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[O:18])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 222413382-Methylpropyl 2-[[(3-methoxyphenyl)thio]methyl]-6-methylbenzoate

Product 1

HCID 22241506HCID 22241506, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1.3 mL, 1.0 M in dichloromethane, 1.3 mmol) is added to a solution of isobutyl 2-[3-(methoxy)-phenylsulfanylmethyl]-6-methyl-benzoate (194 mg, 0.56 mmol, example 82) in dichloromethane (3 mL) at 0° C. and then the reaction is stirred at room temperature 3 h. The reaction is then partitioned between sodium bicarbonate solution and ethyl acetate. The organic phase is dried over magnesium sulfate, concentrated and purified by column chromatography (silica, 15% ethyl acetate in hexanes) to provide the title compound. MS (EI) 330 (M)+.

Workup

  1. customThe reaction is then partitioned between sodium bicarbonate solution and ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. concentrationconcentrated
  4. custompurified by column chromatography (silica, 15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-86c9f63322d94000a45811fb76d4dbd6
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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