1-Chloro-4-(chloromethyl)benzene → HCID 10523286, compound

HRID 1901792

Reaction equation

HRID 1901792 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=3)[C:11]([CH2:20][C:21]([OH:23])=[O:22])=[C:10]2[CH3:24])=[CH:4][CH:3]=1.[CH2:25](OC(=O)CC1C2C(=CC=C(OC)C=2)NC=1C)[CH3:26].[H-].[Na+].ClC1C=CC(CCl)=CC=1>>[CH2:25]([O:22][C:21](=[O:23])[CH2:20][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[N:9]([CH2:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:10]=1[CH3:24])[CH3:26]

Participants

5

Reactant 4

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 40598951-(4-Chlorobenzyl)-5-methoxy-2-methylindole-3-acetic acidHCID 10729163Ethyl (5-methoxy-2-methyl-1H-indol-3-yl)acetate

Product 1

HCID 10523286HCID 10523286, compound

Procedure

1-[(4-Chlorophenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acid. The procedure in Example 63, Part B, was used to react 1.35 g (5.5 mmol) of 5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester with 240 mg (6 mmol) of 60% NaH/mineral oil and 970 mg (6 mmol) of p-chlorobenzyl chloride to give 1.4 g of 1-[(4-chlorophenyl)methyl]-2-methyl-5-methoxy-1H-indole-3-acetic acid ethyl ester that had been chromatographed on silica (20% ether/hexane→35% ether/hexane). This ester was hydrolyzed with 3 mL of 5N NaOH to give 1.23 g of crude 1-[(4-chlorophenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acid.

Sources & evidence

ORD record
ord-4e4fdb465f8e449dae485fea100ecccb
Source dataset
uspto-grants-1996_11
Patent number
US05578634

Linked notes

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