Sodium Chloride → HCID 86594350, compound

HRID 351190Notes

Reaction equation

HRID 351190 reaction equation
C[O:2][C:3]1[CH2:4][C:5]([S:12]([C:15]2([CH2:23][CH2:24][Cl:25])[CH:20]=[CH:19][CH:18]=[C:17]([O:21]C)[CH2:16]2)(=[O:14])=[O:13])([CH2:9][CH2:10][Cl:11])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br.[Na+].[Cl-]>C(Cl)Cl>[OH:2][C:3]1[CH2:4][C:5]([S:12]([C:15]2([CH2:23][CH2:24][Cl:25])[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH2:16]2)(=[O:14])=[O:13])([CH2:9][CH2:10][Cl:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 25134Boron tribromideHCID 86594351HCID 86594351, compound

Product 1

HCID 86594350HCID 86594350, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 6 (8.95 mmol, 2.1 g) in dry DCM (50 cm3) was added 1M BBr3 (27 mmol, 27 cm3 ) in DCM at 0° C. The solution was allowed to reach 20° C. over night, poured into ice water (100 cm3) and stirred for 1.5 h. The aqueous layer was saturated with NaCl and extracted with DCM. The combined organic layers were dried over MgSO4. Filtration and removal of the solvent gave 7 as a white solid (7.8 mmol, 1.72 g, 87%). An analytical sample was obtained by recrystallisation from DCM (mp: 107.6° C.).

Workup

  1. waitto reach 20° C. over night
  2. extractionextracted with DCM
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationFiltration and removal of the solvent

Sources & evidence

ORD record
ord-b87202d407854a1daa6dde829ba82fe0
Source dataset
uspto-grants-2007_02
Patent number
US07183367B2

Reaction notes

Loading…