Benzyl Bromide → HCID 59600091, compound

HRID 2266943Notes

Reaction equation

HRID 2266943 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].C(O[C:20]1[CH:21]=[C:22]([CH:31]=[C:32]([N+]([O-])=O)[CH:33]=1)[C:23](OCCC(C)C)=O)CC(C)C.[CH2:37](Br)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:37]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([O:7][CH2:23][C:22]1[CH:21]=[CH:20][CH:33]=[CH:32][CH:31]=1)=[O:6])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 8203933-Hydroxy-5-nitrobenzoic acid2×HCID 58060846iso-Pentyl 3-iso-pentyloxy-5-nitrobenzoate

Product 1

HCID 59600091HCID 59600091, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 12 was prepared from 3-hydroxy-5-nitrobenzoic acid (8), following the same protocol as for the synthesis of iso-pentyl 3-iso-pentyloxy-5-nitrobenzoate (9). Scale: 2 g (10.9 mmol) 8; 5.2 mL (43.6 mmol) benzyl bromide; 6.03 g (43.6 mmol) K2CO3; 15 mL DMF anhydrous. Crude yield: 6.5 g dark red oil. Column chromatography (hexanes/ethyl acetate, 9:1, Rf=0.5), purified yield: 2.58 g white solid (65%). 1H NMR (CDCl3) δ 8.49 (dd, J1=1.4 Hz, J2=2.0 Hz, 1H), 8.01-7.98 (m, 2H), 7.49-7.34 (m, 10H), 5.41 (s, 2H, PhCH2), 5.19 (s, 2H, PhCH2).

Workup

  1. customColumn chromatography (hexanes/ethyl acetate, 9:1, Rf=0.5), purified yield: 2.58 g white solid (65%)

Sources & evidence

ORD record
ord-a899cb3967fc486696181e8bb7f34da3
Source dataset
uspto-grants-2010_12
Patent number
US07858737B2

Reaction notes

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