Boron tribromide → HCID 22171265, compound

HRID 1866180Notes

Reaction equation

HRID 1866180 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)=[O:4].B(Br)(Br)Br>ClCCl>[F:24][C:2]([F:1])([F:23])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)=[O:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22171566HCID 22171566, compound

Product 1

HCID 22171265HCID 22171265, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under nitrogen at 4° C., to a solution of 2,2,2-trifluoro-N-[2-[4-[(4-methoxyphenyl)thio]phenyl]ethyl]-acetamide (1.5 g) in dichloromethane (15 ml) was added 1M boron tribromide in dichloromethane (10.5 ml), and the mixture was stirred at room temperature for 15 hours. The mixture was evaporated under reduced pressure. The residue was dissolved in a mixture of dichloromethane and saturated aqueous sodium bicarbonate. After separation, the organic layer was dried over magnesium sulfate and evaporated under reduced pressure to give 2,2,2-trifluoro-N-[2-[4-[(4-hydroxyphenyl)thio]phenyl]ethyl]acetamide (1.42 g).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in a mixture of dichloromethane and saturated aqueous sodium bicarbonate
  3. customAfter separation
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1e1839fb318f41bd8e90ab7f928c199b
Source dataset
uspto-grants-2009_12
Patent number
US07629366B2

Reaction notes

Loading…