Benzyl Bromide → HCID 86755712, compound

HRID 1873205Notes

Reaction equation

HRID 1873205 reaction equation
[OH:1][C:2]1[C:14]2[S:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[C:10]=2[C:9]([C:19]2[CH:37]=[C:36]([Br:38])[C:22]([O:23][C@H:24]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:25]([O:27][CH3:28])=[O:26])=[C:21]([Br:39])[CH:20]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[CH2:40](Br)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CN(C)C=O>[CH2:40]([O:1][C:2]1[C:14]2[S:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[C:10]=2[C:9]([C:19]2[CH:37]=[C:36]([Br:38])[C:22]([O:23][CH:24]([CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:25]([O:27][CH3:28])=[O:26])=[C:21]([Br:39])[CH:20]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 53737468HCID 53737468, compound

Product 1

HCID 86755712HCID 86755712, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-2-[4-(6-hydroxy-benzo[b]naphtho[2,3-d]thiophen-11-yl]-2,6-dibromo-phenoxy]-3-phenyl-propionic acid, methyl ester (0.50 g, 0.755 mmol) in dry N,N-dimethylformamide (5 mL) was added benzyl bromide (0.27 mL, 2.27 mmol, 3 eq) dropwise at room temperature under a dry nitrogen atmosphere. After stirring about 17 hours the reaction was quenched with water (50 mL) and the organics were extracted with ether. The extracts were washed with water, and brine and combined with silica gel. The solvent was removed and the adsorbate was flash chromatographed (97/3 petroleum ether/ethyl acetate) and the solvents chased with benzene and petroleum ether to provide the title compound as a pale yellow solid (0.572 g, 84%): NMR (CDCl3); δ8.30 (ddd, J=8, 1, 1 Hz, 1 H), 7.82 (ddd, J=8,1,1 Hz, 1 H), 7.68 (ddd, J=8, 1, 1 Hz, 2 H), 7.62 (dd, J=3, 2 Hz, 2 H), 7.60-7.55 (m, 2 H), 7.51-7.26 (m, 10 H), 7.16 (ddd, J=8, 7,1 Hz, 1 H), 6.81 (ddd, J=8, 1, Hz, 1 H), 5.34 (s, 2 H), 5.25 (dd, J=6, 2 Hz, 1 H), 3.76 (s, 3 H), 3.59 (septet, J =Hz, 2 H); MS (EI): [M+], 2 bromine isotope pattern, 750 (2%), 752 (3.5%), 754 (2.5%); Anal Calc. for C39H28Br2O4S: C, 62.25, H, 3.75, N, 0.00; Found C, 61.66, H, 3.53, N, 0.25.

Workup

  1. customwas quenched with water (50 mL)
  2. extractionthe organics were extracted with ether
  3. washThe extracts were washed with water, and brine
  4. customThe solvent was removed
  5. customchromatographed (97/3 petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-8f945bb09f17483692b5320165934f88
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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