Bromine → HCID 87322888, compound

HRID 2425280Notes

Reaction equation

HRID 2425280 reaction equation
[Br:1]Br.[F:3][C:4]([C:14]([F:32])([F:31])[C:15]([F:30])([F:29])[C:16]([F:28])([F:27])[C:17]([F:26])([F:25])[C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])([C:6]1[S:7][C:8](F)=[C:9]([F:12])[C:10]=1[F:11])[OH:5].C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:3][C:4]([C:14]([F:32])([F:31])[C:15]([F:30])([F:29])[C:16]([F:28])([F:27])[C:17]([F:26])([F:25])[C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])([C:6]1[S:7][C:8]([Br:1])=[C:9]([F:12])[C:10]=1[F:11])[OH:5]

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 87322988HCID 87322988, compound

Product 1

HCID 87322888HCID 87322888, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromine (0.698 g, 4.37 mmol) was added to a solution of 1 (1.80 g, 4.16 mmol) in CH2Cl2 (15 mL). After stirring overnight at room temperature, the mixture was neutralized with saturated aqueous NaHCO3 solution and extracted with CH2Cl2 (3×20 mL). The organic layers were combined, dried over MgSO4, filtered, and concentrated in vacuo (1.90 g, 89%). 1H NMR (CDCl3): δ 7.02 (d, 1H, 2J=3.7 Hz), 6.97 (d, 1H, 2J=3.8 Hz), 5.46-5.38 (m, 1H), 2.64 (d, 1H, 2J=5.2 Hz); HRMS (EI, 70 eV) m/z: calcd (M+) for C11H4F13BrOS, 509.90; found, 509.8945.

Workup

  1. extractionextracted with CH2Cl2 (3×20 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo (1.90 g, 89%)

Sources & evidence

ORD record
ord-b6f9e9ae6199499c899083a321d84e4b
Source dataset
uspto-grants-2011_06
Patent number
US07964650B2

Reaction notes

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