HCID 67203337, compound → HCID 67202315, compound

HRID 2377940Notes

Reaction equation

HRID 2377940 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:11][C:10]=1[F:21])C1C=CC=CC=1>CO.[Pd]>[F:21][C:10]1[CH:11]=[C:12]([CH2:15][CH2:16][S:17]([CH3:20])(=[O:18])=[O:19])[CH:13]=[CH:14][C:9]=1[OH:8]

Participants

4

Reactant 1

HCID 67203337HCID 67203337, compound

Product 1

HCID 67202315HCID 67202315, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-benzyloxy-2-fluoro-4-(2-methylsulfonyl-ethyl)-benzene (1.5 g, 4.87 mmol) in MeOH (25 mL) was added Pd/C (50 mg). The reaction was stirred under H2 (1 atm) for 3 hours. The solid material was filtrated off and the filtrate was concentrated under vacuum to afford the desired compound (981 mg, 92.4%) as a yellowish solid. The crude compound was used for the next step without further purification. 1H NMR (400 Mz, DMSO-d6) δ 9.73 (s, 1H), 7.14˜7.11 (m, 1H), 6.94˜6.87 (m, 2H), 3.43˜3.37 (m, 2H), 2.98 (s, 3H), 2.95˜2.91 (m, 2H). LCMS 228.2 [MH+].

Workup

  1. filtrationThe solid material was filtrated off
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-de5556cf837a4a238f8ad0846c077a44
Source dataset
uspto-grants-2008_12
Patent number
US07470699B2

Reaction notes

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