Water → HCID 22909967, compound

HRID 1379282

Reaction equation

HRID 1379282 reaction equation
B(Br)(Br)[Br:2].[OH:5][CH:6]1[CH2:10][CH2:9][O:8][C:7]1=O.[F:12][C:13]([F:28])([F:27])[C:14]1[CH:15]=[C:16]([NH:20]C2C=CC=CC=2)[CH:17]=[CH:18][CH:19]=1.O>ClCCCl>[Br:2][CH2:9][CH2:10][CH:6]([OH:5])[C:7]([NH:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([F:28])([F:27])[F:12])[CH:15]=1)=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 75483-(Trifluoromethyl)-N-phenylanilineHCID 25134Boron tribromideHCID 545831alpha-Hydroxy-gamma-butyrolactone

Product 1

HCID 22909967HCID 22909967, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Boron tribromide (11.0 ml, 1.0M solution in dichloromethane) was added dropwise to a stirred solution of 3-hydroxytetrahydrofuran-2-one (1.0 g) and 3-trifluoromethylphenylaniline (1.58 g) in 1,2-dichloroethane (20 ml). The mixture was stirred overnight at room temperature, poured on to water and extracted with dichloromethane. The extracts were washed with hydrochloric acid (2M) and brine, dried over magnesium sulphate, and evaporated under reduced pressure. The residue was chromatographed on silica, using dichloromethane-ethanol (49:1) as eluant, to give the title compound (0.74 g, m.p. 67°-69° C.). NMR (CDCl3): δ 2.3(1H,m); 2.6(1H,m); 3.5(1H,bs); 3.6(2H,dd); 4.5(1H,dd); 7.4(2H,m); 7.7 (1H,d); 7.9(1H,s); 8.7(1H,bs). MS: M+ 325, 327.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extracts were washed with hydrochloric acid (2M) and brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-ef0784d5e22a4363bdfa21ab08973160
Source dataset
uspto-grants-1997_09
Patent number
US05670656

Linked notes

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