4-Bromobenzyl bromide → HCID 53889498, compound

HRID 1265262Notes

Reaction equation

HRID 1265262 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[C:21]([OH:22])=[CH:20][C:19]3[C:18]([CH3:24])([CH3:23])[CH2:17][CH2:16][C:15]([CH3:26])([CH3:25])[C:14]=3[CH:13]=2)=[O:11])=[CH:6][CH:5]=1.[Br:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=1>>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[C:21]([O:22][CH2:33][C:32]3[CH:35]=[CH:36][C:29]([Br:28])=[CH:30][CH:31]=3)=[CH:20][C:19]3[C:18]([CH3:23])([CH3:24])[CH2:17][CH2:16][C:15]([CH3:26])([CH3:25])[C:14]=3[CH:13]=2)=[O:11])=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 685274-Bromobenzyl bromideHCID 10021814HCID 10021814, compound

Product 1

HCID 53889498HCID 53889498, compoundYield 60%

Procedure

The 4-[(3-hydroxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbonyl]benzoic acid methyl ester (from Example 7) was alkylated with 4-bromobenzylbromide as described for Example 60 to give 4-[(3-(4-bromobenzyloxy)-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbonyl]benzoic acid methyl ester (60%): 1H NMR (400 MHz, CDCl3) δ 8.03 (1/2ABq, 2H, J=8.4 Hz, ArH), 7.80 (1/2ABq, 2H, J=8.4 Hz, ArH), 7.46 (s, 1H, ArH), 7.29 (1/2ABq, 2H, J=8.4 Hz, ArH), 6.87 (s, 1H, ArH), 6.81 (1/2ABq, 2H, J=8.4 Hz, ArH), 4.87 (s, 2H, OCH2), 3.97 (s, 3H, OCH3), 1.70 (m, 4H, 2CH2), 1.30 (s, 6H, 2CH3), 1.27 (s, 6H, 2CH3).

Sources & evidence

ORD record
ord-bfd7b91995e5454ebd0107f77370b52c
Source dataset
uspto-grants-2003_04
Patent number
US06545049B1

Reaction notes

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