Bromine → HCID 12972353, compound

HRID 1069209Notes

Reaction equation

HRID 1069209 reaction equation
[Br:1]Br.[CH3:3][C:4]1[S:8][C:7]2[CH:9]=[C:10]3[C:15](=[C:16]([C:17]4[CH:22]=[CH:21][C:20]([O:23][C:24](=[O:26])[CH3:25])=[CH:19][CH:18]=4)[C:6]=2[C:5]=1[CH3:27])[CH:14]=[CH:13][CH:12]=[CH:11]3.S(=O)(O)[O-].[Na+]>ClCCl.[Fe](Cl)(Cl)Cl>[Br:1][C:9]1[C:7]2[S:8][C:4]([CH3:3])=[C:5]([CH3:27])[C:6]=2[C:16]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24](=[O:26])[CH3:25])=[CH:19][CH:18]=2)=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[CH:14]2

Participants

6

Reactant 3

HCID 24408BromineHCID 12972352HCID 12972352, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 12972353HCID 12972353, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of bromine (0.326 mL, 6.15 mmol) in dichloromethane (9 mL) was added dropwise over a 15 minute period to a solution that was stirred in the absence of light of acetic acid 4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenyl ester (1.87 g, 5.41 mmol) and iron (III) chloride (50 mg, 0.31 mmol) in dichloromethane (47 mL) at −78° C. under a dry nitrogen atmosphere. After 10 minutes, a dilute aqueous sodium bisulfite solution was added and the reaction mixture was partitioned between water and ether. The ether phase was washed with brine and concentrated to provide the title compound as a white solid (2.09 g, 91%): mp: 190-191° C.; NMR (DMSO-d6); δ8.20 (d, J=8 Hz, 1H), 7.65 (ddd, J=8, 7, 1, 1H), 7.49 (ddd, J=8, 7, 1 Hz, 1H), 7.43-7.38 (m, 1H), 7.40 (d, J=9 Hz, 2H), 7.30 (d, J=9 Hz, 2H), 2.43 (d, J=1 Hz, 3H), 2.33 (s, 3H), 1.55 (d, J=1 Hz, 3H); MS (EI): 1 bromine isotope pattern 424 (95%, MI), 426 (100%); Anal. Calc. for C22H17BrO2S: C, 62.12; H, 4.03; N, 0.00. Found: C, 62.46; H, 4.05; N, 0.09.

Workup

  1. customthe reaction mixture was partitioned between water and ether
  2. washThe ether phase was washed with brine
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-788840268ac047089d6e7ad3d9ce1c92
Source dataset
uspto-grants-2001_06
Patent number
US06251936B1

Reaction notes

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