Boron tribromide → HCID 54680207, compound

HRID 845813Notes

Reaction equation

HRID 845813 reaction equation
[OH:1][C:2]1[C:3]2[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:4]=2[S:5][C:6]=1[C:7]([NH:9][CH:10]=[C:11]([C:20]1[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=1)[C:12]1[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=1)=[O:8].B(Br)(Br)Br>ClCCl>[OH:1][C:2]1[C:3]2[CH:31]=[C:30]([C:32]([F:35])([F:33])[F:34])[CH:29]=[CH:28][C:4]=2[S:5][C:6]=1[C:7]([NH:9][CH:10]=[C:11]([C:20]1[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=1)[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[O:8]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 54680218HCID 54680218, compound

Product 1

HCID 54680207HCID 54680207, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-50 °C

Procedure

To a solution of 3-hydroxy-N-[2,2-di-(4-methoxyphenyl)ethenyl]-5-trifluoromethylbenzo[b]thiophe ne-2-carboxamide (200 mg) in dichloromethane (30 ml) cooled to -50° C. was added dropwise with stirring N boron tribromide in dichloromethane (2.9 ml). The reaction mixture was stirred at -50° C. for one hour, then the temperature allowed to rise to 0° C., and the reaction quenched by pouring into ice-saturated sodium hydrogencarbonate solution. The yellow solid that separated out was filtered, washed thoroughly with hexane and dried in vacuo to yield 104 mg (55%) of 3-hydroxy-N-[2,2-di-(4-hydroxyphenyl)ethenyl]-5-trifluoromethylbenzo[b]thiophene-2-carboxamide; m/z 471 (M+).

Workup

  1. customto rise to 0° C.
  2. customthe reaction quenched
  3. additionby pouring into ice-saturated sodium hydrogencarbonate solution
  4. customThe yellow solid that separated out
  5. filtrationwas filtered
  6. washwashed thoroughly with hexane
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d625781ad57f4107bd94f633c2459829
Source dataset
uspto-grants-1988_07
Patent number
US04760086

Reaction notes

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