Boron tribromide → HCID 13922876, compound

HRID 979573Notes

Reaction equation

HRID 979573 reaction equation
CO[CH2:3][CH2:4][C:5]1[CH:17]=[CH:16][C:8]2[S:9][C:10]([S:12](=[O:15])(=[O:14])[NH2:13])=[CH:11][C:7]=2[CH:6]=1.B(Br)(Br)[Br:19]>C(Cl)Cl.O>[Br:19][CH2:3][CH2:4][C:5]1[CH:17]=[CH:16][C:8]2[S:9][C:10]([S:12](=[O:15])(=[O:14])[NH2:13])=[CH:11][C:7]=2[CH:6]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 13922874HCID 13922874, compound

Product 1

HCID 13922876HCID 13922876, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(2-methoxyethyl)-2sulfamoylbenzo[b]thiophene (8.3 g, 0.031 mol) in 550 ml of methylene chloride at -78° C. was added dropwise under nitrogen, 100 ml of a solution of boron tribromide (BBr3) (lM in hexane, 0.1 mol). The reaction was stirred at room temperature overnight (15 hours) following the addition. The mixture was cooled and diluted with 100 ml of cold water. The aqueous phase was separated and extracted 2X with methylene chloride. The original organic phase and the extracts were combined, dried, filtered and concentrated to dryness to yield 8.3 g (86%) of product with m.p. 118°-120° C.

Workup

  1. additionthe addition
  2. temperatureThe mixture was cooled
  3. customThe aqueous phase was separated
  4. extractionextracted 2X with methylene chloride
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-18c795fe124847eeb06521b5d65eb61d
Source dataset
uspto-grants-1987_05
Patent number
US04668697

Reaction notes

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