Boron tribromide → HCID 13922876, compound

HRID 2232356Notes

Reaction equation

HRID 2232356 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)-2-sulfamoylbenzo[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) (1M 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 2× 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 2× with methylene chloride
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ffb896b0092645cba50f5f06ab8dd1b1
Source dataset
uspto-grants-1988_11
Patent number
US04788192

Reaction notes

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