Boron tribromide → HCID 9823190, compound

HRID 2305303Notes

Reaction equation

HRID 2305303 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11](=[O:23])[C:12]3[CH:17]=[CH:16][C:15]([CH:18]=[CH:19][C:20]([OH:22])=[O:21])=[CH:14][CH:13]=3)=[C:9]([C:24]3[CH:29]=[CH:28][C:27]([O:30]C)=[CH:26][CH:25]=3)[S:8][C:7]=2[CH:32]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11](=[O:23])[C:12]3[CH:13]=[CH:14][C:15](/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21])=[CH:16][CH:17]=3)=[C:9]([C:24]3[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=3)[S:8][C:7]=2[CH:32]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 54136870HCID 54136870, compound

Product 1

HCID 9823190HCID 9823190, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

To a −5° C. solution of 6-methoxy-3-[4-(2-carboxyvinyl)benzoyl]-2-(4-methoxyphenyl)benzo[b]thiophene (900 mg, 2.0 mmol) in 40 mL of anhydrous CH2Cl2 under N2 was added BBr3 (0.76 mL, 8.0 mmol) slowly via syringe. After warming to 5° C., the mixture was stirred for 1 h at 5° C., then quenched by pouring into ice water (100 mL). The mixture was extracted with EtOAc (3×100 mL). The organic was then dried (Na2SO4) and concentrated in vacuo to a solid residue that was chromatographed (SiO2, 1% MeOH/CHCl3) to provide 730 mg (86%) of (E)-6-hydroxy-3-[4-(2-carboxyvinyl)benzoyl]-2-(4-hydroxyphenyl)benzo[b]thiophene as a yellow solid. mp 155-160° C. 1H NMR (DMSO-d6) δ 12.55 (bs, 1H), 9.81 (s, 1H), 9.73 (s, 1H), 7.67 (s, 4H), 7.54 (d, J=16.0 Hz, 1H), 7.40 (d, J=9.0 Hz, 1H), 7.30 (d, J=2.5 Hz, 1H), 7.18 (d, J=9.0 Hz, 2H), 6.89 (dd, J=9.0, 2.5 Hz, 1H), 6.65 (d, J=9.0 Hz, 2H), 6.58 (d, J=16.0 Hz, 1H). FD mass spec: 416. Anal. Calcd. for C24H16O5S: C, 69.22; H, 3.87. Found: C, 68.95; H, 3.73.

Workup

  1. customquenched
  2. additionby pouring into ice water (100 mL)
  3. extractionThe mixture was extracted with EtOAc (3×100 mL)
  4. dry with materialThe organic was then dried (Na2SO4)
  5. concentrationconcentrated in vacuo to a solid residue that
  6. customwas chromatographed (SiO2, 1% MeOH/CHCl3)

Sources & evidence

ORD record
ord-0412e3cb32a443ceb4a751948422f2fc
Source dataset
uspto-grants-2002_08
Patent number
US06440958B1

Reaction notes

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