Boron tribromide → HCID 67052221, compound

HRID 1918223Notes

Reaction equation

HRID 1918223 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([O:33]C)=[C:10]([CH:32]=1)[C:11]([NH:13][C:14]1[C:15]([C:28]([O:30][CH3:31])=[O:29])=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([F:26])[C:20]=2[F:27])[S:17][CH:18]=1)=[O:12]>ClCCl>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([OH:33])=[C:10]([CH:32]=1)[C:11]([NH:13][C:14]1[C:15]([C:28]([O:30][CH3:31])=[O:29])=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([F:26])[C:20]=2[F:27])[S:17][CH:18]=1)=[O:12]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67052291HCID 67052291, compound

Product 1

HCID 67052221HCID 67052221, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an atmosphere of argon, BBr3 (1 mL of a 1 M solution in dichloromethane) was added dropwise to ester 394 (82 mg, 182 μmol) at −78° C. The reaction was stirred for 1 h then quenched with a saturated solution of NaHCO3 (1 mL). The mixture was extracted with dichloromethane (3×5 mL) and combined extracts dried over Na2SO4 and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-50% ethyl acetate in hexane) provided 395 (74.1 mg, 93%) as a solid: LRESIMS m/z 438.0 [M+H]+, calcd. for C20H15Cl1F2N1O4S1 438.0.

Workup

  1. customthen quenched with a saturated solution of NaHCO3 (1 mL)
  2. extractionThe mixture was extracted with dichloromethane (3×5 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-40ff1464dcb440618d95888a92d1b038
Source dataset
uspto-grants-2013_12
Patent number
US08618307B2

Reaction notes

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