Water → HCID 10790583, compound

HRID 840624Notes

Reaction equation

HRID 840624 reaction equation
[Br:1]Br.[CH2:3]([C:10]1[S:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[C:11]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])(=O)C.[K+].O>C(O)(=O)C>[CH2:3]([C:10]1[S:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[C:11]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[CH:27][C:28]([OH:31])=[C:29]([Br:1])[CH:30]=2)=[CH:21][CH:20]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 517044Potassium AcetateHCID 10548559HCID 10548559, compound

Product 1

HCID 10790583HCID 10790583, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Bromine (1.47 mL, 28.69 mmol) in acetic acid (50 mL) was added dropwise over a 30 minutes period into a cold (5° C.) mixture of 4′-(2-benzyl-benzo[b]thiophen-3-yl)-biphenyl-4-ol (7.5 g, 19.13 mmol), potassium acetate (18.6 g, 190.13 mmol), and acetic acid (200 mL). After the addition the mixture was poured into water, and extracted with ethyl ether. The organic extracts were washed with aqueous sodium bisulfite and dried over MgSO4. Evaporation and purification by flash chromatography on silica gel (hexanes/EtAOc/CH2Cl2 3:1:1) gave 4′-(2-benzyl-benzo[b]thiophen-3-yl)-3-bromo-biphenyl-4-ol as a light yellow solid (2.4 g): mp 54-56° C. MS m/e 477 (M+);

Workup

  1. additionAfter the addition the mixture
  2. extractionextracted with ethyl ether
  3. washThe organic extracts were washed with aqueous sodium bisulfite
  4. dry with materialdried over MgSO4
  5. customEvaporation and purification by flash chromatography on silica gel (hexanes/EtAOc/CH2Cl2 3:1:1)

Sources & evidence

ORD record
ord-c01b37cb5ec341c79307ad1822e0643c
Source dataset
uspto-grants-2002_04
Patent number
US06369072B2

Reaction notes

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