Water → HCID 59378879, compound

HRID 2201630Notes

Reaction equation

HRID 2201630 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[C:8](=[O:13])[CH2:7][CH2:6][CH2:5]2.C(N(CC)CC)C.[F:21][C:22]1[CH:23]=[C:24]([SH:28])[CH:25]=[CH:26][CH:27]=1.O>CC(OC)(C)C>[F:12][C:10]1[CH:11]=[C:2]([S:28][C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([F:21])[CH:23]=2)[CH:3]=[C:4]2[C:9]=1[C:8](=[O:13])[CH2:7][CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 75710m-FluorobenzenethiolHCID 552745816,8-Difluoro-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 59378879HCID 59378879, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of 6,8-difluoro-3,4-dihydro-2H-naphthalen-1-one (50 g) in N,N′dimethylacetamide (100 ml) was treated with triethylamine (38.2 ml), followed by 3-fluorothiophenol (28.2 ml), keeping the temperature below 20° C. The reaction mixture was allowed to stir at ambient temperature for 18 hours. The reaction was diluted with MTBE (70 ml) and cooled on an ice-bath. Water (300 ml) was slowly added (keeping temperature below 25° C.) and the mixture aged for 1 hour. The product was collected by filtration and washed with water and cyclohexane, and dried to afford 8-fluoro-6-(3-fluoro-phenylsulfanyl)-3,4-dihydro-2H-naphthalen-1-one as a pale yellow solid yield (53.5 g, 95% pure by HPLC): MP=126.0-126.9° C.; MS (M+1)=291; H1 NMR (300 MHz): δ (DMSO): 1.97 (2H, pen, J=6.03 Hz), 2.55 (2H, t, J=6.03 Hz), 2.88 (2H, t, J=6.03), 6.84 (1H, dd, J=1.88, 12.06 Hz) 7.01 (1H, d, J=1.03 Hz), 7.31-7.44 (3H, m), 7.52-7.59 (1H, dd/d, J=6.03, 6.41 Hz).

Workup

  1. customthe temperature below 20° C
  2. temperaturecooled on an ice-bath
  3. waitthe mixture aged for 1 hour
  4. filtrationThe product was collected by filtration
  5. washwashed with water and cyclohexane
  6. customdried

Sources & evidence

ORD record
ord-6e61b3b4d6cb42d4995f6c2a01d6568d
Source dataset
uspto-grants-2016_06
Patent number
US09365494B2

Reaction notes

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