Hexane → HCID 10810351, compound

HRID 865747Notes

Reaction equation

HRID 865747 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:27])[C:20]([OH:26])([CH3:25])[C:21]([F:24])([F:23])[F:22])=[CH:14][CH:13]=1)(=[O:11])=[O:10].B(Br)(Br)Br.CCCCCC>C(Cl)Cl.C(OCC)(=O)C>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([C:12]1[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:27])[C:20]([OH:26])([CH3:25])[C:21]([F:24])([F:22])[F:23])=[CH:16][CH:17]=1)(=[O:10])=[O:11]

Participants

6

Reactant 3

HCID 8058HexaneHCID 25134Boron tribromide2×HCID 10644842HCID 10644842, compound

Product 1

HCID 10810351HCID 10810351, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of N-[4-(2-methoxyphenylsulfonyl)phenyl]3,3,3-trifluoro-2-hydroxy-2-methylpropanamide (1.14 g, 2.8 mmol) in dry methylene chloride (30 mL) was added boron tribromide (8.5 mL of a 1.0M solution of boron tribromide in methylene chloride, 8.5 mmol). The resulting solution was stirred at room temperature for 3 hours, diluted with methylene chloride (50 mL) and washed with water. The organic layer was dried (MgSO4) and concentrated in vacuo to yield an off-white solid which was dissolved in ethyl acetate (10 mL) and dropped into hexane (300 mL). Collection of the precipitate by filtration yielded the title propanamide as a white solid (0.84 g, 77%); mp 184°-186° C. 1H-NMR (250 MHz, d6-DMSO): 1.57 (s, 3H, CH3) 6.90 (d, 1H, J=8.3 Hz, aromatic) 7.01 (t, 1H, J=7.5 Hz, aromatic) 7.50 (m, 1H, aromatic) 7.56 (s, 1H, OH) 7.85-7.97 (m, 5H, aromatic) 10.37 (s, 1H, NH) 10.74 (s, 1H, OH). MS (CI, CH4): 390 (M+1).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto yield an off-white solid which
  5. customCollection of the precipitate
  6. filtrationby filtration

Sources & evidence

ORD record
ord-c90fd4b895b84a799f2f4d461c994591
Source dataset
uspto-grants-1996_10
Patent number
US05567735

Reaction notes

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