4-Bromo-m-cresol → HCID 66643648, compound

HRID 1170961Notes

Reaction equation

HRID 1170961 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[CH3:10][O:11][CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][C:15]=1[CH:22]([CH3:24])[CH3:23]>C(OCC)(=O)C>[CH3:10][O:11][CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=2[CH3:9])=[CH:16][C:15]=1[CH:22]([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 728574-Bromo-m-cresolHCID 86052179HCID 86052179, compound

Product 1

HCID 66643648HCID 66643648, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Intermediate 4-(4′-methoxymethoxy-3′-iso-propylbenzyl)-3-methyl-phenol was prepared from 4-bromo-3-methyl-phenol (J. Med. Chem. 1980, 12, 1350) and 4-methoxymethoxy-3-iso-propylbenzaldehyde according to the procedure described in G. Chiellini et al. Biorg. Med. Chem. Lett. 2000, 10, 2607 and transformed into the title compound by the procedure used for the synthesis of compound 7. 1H NMR (300 MHz, DMSO-d6): δ 9.04 (s, 1 H), 7.02-6.99 (d, J=8.7 Hz, 1 H), 6.92 (s, 1 H), 6.81-6.76 (m, 2 H), 6.67 (s, 2 H), 4.03 (d, J=10.5 Hz, 2 H), 3.76 (s, 2 H), 3.16-3.14 (m, 1 H), 2.19 (s, 3 H), 1.14-1.12 (d, J=6.9 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate; Rf=0.11;

Sources & evidence

ORD record
ord-fc9fe50efdcd4ceeb3715c86c629bf98
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

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