Dichloromethane → HCID 10045621, compound

HRID 2181857Notes

Reaction equation

HRID 2181857 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([S:11]([N:14]2[CH:27]([CH3:28])[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([F:29])[CH:25]=3)[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]2=3)(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9]C.C1CCCCC=1.B(Br)(Br)Br.ClCCl>>[F:29][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[C:20]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:14]([S:11]([C:5]1[CH:4]=[C:3]([OH:2])[C:8]([OH:9])=[CH:7][CH:6]=1)(=[O:13])=[O:12])[CH:27]2[CH3:28]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 22482393HCID 22482393, compound

Product 1

HCID 10045621HCID 10045621, compoundYield 50%

Procedure

The title compound was prepared from 5-[(3,4-dimethoxyphenyl)sulfonyl]-8-fluoro-6-methyl-5,6-dihydrophenanthridine (0.50 g, 1.2 mmol), cyclohexene (4.4 mL, 44 mmol), and 1 M boron tribromide in dichloromethane (14.5 mL, 14.5 mmol) according to the procedure and in the same manner as described in Example 47, Step b. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:1 to 7:3 gradient), followed by re-crystallization from a mixture of dichloromethane-hexane (2×), to yield 4-[(8-fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]benzene-1,2-diol as a homogeneous solid (0.23 g, 50%), m.p. 165-170° C.;

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (1:1 to 7:3 gradient)
  3. customfollowed by re-crystallization from a mixture of dichloromethane-hexane (2×)

Sources & evidence

ORD record
ord-71cd825424a840ed8c4a04b5feccd82d
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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