Bromine → HCID 18687831, compound

HRID 1873212Notes

Reaction equation

HRID 1873212 reaction equation
C(=O)=O.C(Cl)(Cl)(Cl)Cl.[CH:9]1[C:17]2[C:16]3[C:18]([C:26]4[C:27]([F:34])=[C:28]([OH:33])[C:29]([F:32])=[CH:30][CH:31]=4)=[C:19]4[C:24](=[CH:25][C:15]=3[S:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)[CH:23]=[CH:22][CH:21]=[CH:20]4.[Br:35]Br>C(Cl)Cl>[Br:35][C:25]1[C:15]2[S:14][C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:17]=3[C:16]=2[C:18]([C:26]2[C:27]([F:34])=[C:28]([OH:33])[C:29]([F:32])=[CH:30][CH:31]=2)=[C:19]2[C:24]=1[CH:23]=[CH:22][CH:21]=[CH:20]2

Participants

5

Reactant 3

HCID 24408BromineHCID 18687793HCID 18687793, compoundHCID 86602444Carbontetrachloride dry-ice

Product 1

HCID 18687831HCID 18687831, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a cold (-23° C. dry ice/carbon tetrachloride bath) stirred solution of 3-(benzo [b]naphtho[2,3-d]thiophen-11-yl)-2,6 difluoro-phenol (1.38 g, 3.81 mmol) in methylene chloride (35 mL) was added a solution of bromine (0.22 mL, 4.19 mmol) in methylene chloride (7 mL) dropwise, very slowly, over a period of 28 minutes. After stirring an additional 1.5 h the reaction was quenched with dilute sodium bisulfite and the organics were extracted with ether. The extract was concentrated to give a yellow solid (1.64 g, 98% crude yield). A small portion was taken up in methylene chloride and combined with silica gel. The solvent was removed and the adsorbate was flash chromatographed (85/15 petroleum ether/ethyl acetate) to give the title compound as an off white solid: mp 180-182° C.; NMR (400 MHz, DMSO-d6); δ10.64 (s, 1 H), 8.30 (d, J=9 Hz, 1 H), 8.09 (d, J=9 Hz, 1 H), 7.82-7.78 (m, 1 H), 7.64-7.51 (m, 3 H), 7.42-7.37 (m, 1 H), 7.33-7.29 (m, 1 H), 6.96-6.91 (m, 1 H), 6.81-6.78 (m, 1 H); MS (FAB): (M-H): one bromine pattern observed; 439/441 (8%); Anal. Calc. for C22H11BrF2OS: C, 59.88, H, 2.51, N, 0.00%. Found: C, 59.82, H, 2.59, N, 0.06.

Workup

  1. customwas quenched with dilute sodium bisulfite
  2. extractionthe organics were extracted with ether
  3. concentrationThe extract was concentrated
  4. customto give a yellow solid (1.64 g, 98% crude yield)
  5. customThe solvent was removed
  6. customchromatographed (85/15 petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-cc85c917cfa94b4e8c28c5d668d1caf5
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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