Thiophenol → 8-fluoro-6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one

HRID 2201628ノート

反応式

HRID 2201628 の反応式
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.[C:21]1([SH:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCCCCCC>CN(C)C(=O)C.O>[F:12][C:10]1[CH:11]=[C:2]([S:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:3]=[C:4]2[C:9]=1[C:8](=[O:13])[CH2:7][CH2:6][CH2:5]2

参加物

7

反応物 4

HCID 7969ThiophenolHCID 8471TriethylamineHCID 8900HeptaneHCID 552745816,8-Difluoro-3,4-dihydronaphthalen-1(2H)-one

生成物 1

HCID 590217698-fluoro-6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one収率 79%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒

実験手順

A solution of 6,8-difluoro-3,4-dihydro-2H-naphthalen-1-one (1.58 kg) in N,N-dimethylacetamide (4.65 liters) was treated with triethylamine (877 g) and thiophenol (954.9 g) at 20° C. and the reaction mixture was stirred for 19 hours. The reaction mixture was treated with heptane (2.38 liters.), followed by water (9.5 liters) and the precipitate was isolated by filtration and the resulting slurry washed with twice with heptane (790 ml each time), three times with water (1.0 liters each time) and five times with cyclohexane (1.0 liters, each time). The slurry was dried to give 8-fluoro-6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one (1.86 kg, 79% yield) with a purity of 96.2% by HPLC, together with 3.6% yield of the isomer 6-fluoro-8-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one: MP=111.7-112.7° C.; MS (M+1)=273; H1 NMR (300 MHz): δ(DMSO): 1.96 (2H, p, J=6.4 Hz), 2.53 (2H, t, J=6.03 Hz), 2.84 (2H, t, J=6.03 Hz), 6.69 (1H, dd, J=1.51, 12.06 Hz), 6.91 (1H, d, J=1.13 Hz), 7.5-7.61 (5H, m, Phenyl).

後処理

  1. customthe precipitate was isolated by filtration
  2. washthe resulting slurry washed with twice with heptane (790 ml each time), three times with water (1.0 liters each time) and five times with cyclohexane (1.0 liters
  3. customThe slurry was dried

出典と根拠

ORDレコード
ord-79924d0183024a72b3e4ea9c4e36d57e
出典データセット
uspto-grants-2016_06
特許番号
US09365494B2

反応ノート

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