Boron tribromide → HCID 9847371, compound

HRID 2211381Notes

Reaction equation

HRID 2211381 reaction equation
[CH2:1]([C:5]1[CH:28]=[C:27]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C:26]([O:36]C)=[CH:25][C:6]=1[O:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][CH2:19][C:20]([O:22]CC)=[O:21])[CH2:2][CH2:3][CH3:4].B(Br)(Br)Br>ClCCl>[CH2:1]([C:5]1[CH:28]=[C:27]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C:26]([OH:36])=[CH:25][C:6]=1[O:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 19375840HCID 19375840, compound

Product 1

HCID 9847371HCID 9847371, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 3-(2-(3-(2-butyl-4-(4-fluorophenyl)-5-methoxyphenoxy)propoxy)phenyl)propionate in dichloromethane was treated with 2 equivalents of boron tribromide at -75° C. The mixture was stirred without cooling for 18 hours, washed with water, dried, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with dichloromethane/methanol to provide the desired title product in 56% yield. NMR.

Workup

  1. temperaturewithout cooling for 18 hours
  2. washwashed with water
  3. customdried
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with dichloromethane/methanol

Sources & evidence

ORD record
ord-93245c03957149afa65d5565cf4c8b7a
Source dataset
uspto-grants-1995_10
Patent number
US05462954

Reaction notes

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