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

HRID 2108600Notes

Reaction equation

HRID 2108600 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. 12:1350 (1980)) and 4-methoxymethoxy-3-iso-propylbenzaldehyde according to the procedure described in Chiellini et al., Bioorg. Med. Chem. Lett. 10:2607 (2000) 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, 1H), 7.02-6.99 (d, J=8.7 Hz, 1H), 6.92 (s, 1H), 6.81-6.76 (m, 2H), 6.67 (s, 2H), 4.03 (d, J=10.5 Hz, 2H), 3.76 (s, 2H), 3.16-3.14 (m, 1H), 2.19 (s, 3H), 1.14-1.12 (d, J=6.9 Hz, 6H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate; Rf=0.11;

Sources & evidence

ORD record
ord-aef11faffd3d4dc5ab42861eea08197e
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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