Menadione → HCID 67057845, compound

HRID 1528021Notes

Reaction equation

HRID 1528021 reaction equation
C[C:2]1[C:12](=[O:13])[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:4](=[O:5])[CH:3]=1.[F:14][C:15]([F:28])([F:27])[O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24](O)=O)=[CH:19][CH:18]=1.[K+].[Br-]>CC(=O)OCC>[CH3:2][C:3]1[C:4](=[O:5])[C:6]2[C:11]([C:12](=[O:13])[C:24]=1[CH2:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][C:15]([F:28])([F:27])[F:14])=[CH:18][CH:19]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

5

Reactant 3

HCID 4055MenadioneHCID 253877Potassium BromideHCID 27773192-[4-(Trifluoromethoxy)phenyl]acetic acid

Product 1

HCID 67057845HCID 67057845, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

As starting materials for the coupling reaction menadione and 4-(trifluoromethoxy)phenylacetic acid were used. Synthesis is realized according to the general procedure described in general procedure of example 1. After chromatography on silica gel (petroleum ether:CH2Cl2=1:1, UV), 494 mg (1.43 mmol, 78% yield) of P_TM97 were isolated as yellow solid. Melting point: 64-65° C. —1H-NMR (300 MHz, CDCl3): δ=8.03-8.10 (m, 2H), 7.65-7.71 (m, 2H), 7.34 (d, 3J=8.74 Hz, 2H), 7.09 (d, 3J=8.08 Hz, 2H), 4.01 (s, 2H), 2.23 (s, 3H). —13C-NMR (75 MHz, CDCl3): δ=185.17 (Cq), 184.52 (Cq), 147.42 (Cq), 144.72 (Cq), 144.57 (Cq), 136.76 (Cq), 133.57 (CH), 132.07 (Cq), 131.92 (Cq), 129.87 (CH), 126.47 (CH), 126.33 (CH), 121.15 (CH), 120.44 (q, 1JCF=256.91 Hz), 31.78 (CH2), 13.27 (CH3). —EI MS (70 eV, m/z (%)): 346.0 ([M]+, 32), 331.1 (100), 261.1 (8), 175.1 (71), 76.0 (10), 28.0 (49). —IR (KBr): 3077 cm−1 (w), 3047 (w), 3021 (w), 3003 (w), 2963 (w), 2948 (w), 2853 (w), 2143 (w), 2004 (w), 1975 (w), 1901 (w), 1876 (w), 1664 (vs), 1620 (m), 1596 (s), 1508 (s), 1446 (w), 1435 (w), 1378 (m), 1333 (s), 1297 (vs), 1271 (vs), 1217 (vs), 1188 (vs), 1166 (vs), 1111 (m), 1019 (w), 976 (m), 793 (w), 770 (w), 708 (s), 692 (w). —EA: obs. C, 65.78%; H, 3.98%, calcd. C, 65.90%; H, 3.78% for C19H13F3O3.

Workup

  1. customSynthesis
  2. customAfter chromatography on silica gel (petroleum ether:CH2Cl2=1:1, UV), 494 mg (1.43 mmol, 78% yield) of P_TM97 were isolated as yellow solid

Sources & evidence

ORD record
ord-93549efb40e7462e9fac3703fe62a3b1
Source dataset
uspto-grants-2015_07
Patent number
US09090549B2

Reaction notes

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