1,2-Dichlorobenzene → HCID 86685136, compound

HRID 1913032Notes

Reaction equation

HRID 1913032 reaction equation
C([O:8][C@H:9]1[C@H:15]([O:16]CC2C=CC=CC=2)[C@@H:14]([O:24]CC2C=CC=CC=2)[C@:13]2([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]4[CH:42]=[CH:43][C:44]5[O:48][CH2:47][CH2:46][C:45]=5[CH:49]=4)[CH:34]=3)[O:32][C@@:10]1([CH2:50][OH:51])[CH2:11][O:12]2)C1C=CC=CC=1.ClC1C=CC=CC=1Cl>[Pd]>[Cl:39][C:36]1[CH:37]=[CH:38][C:33]([C@@:13]23[O:32][C@@:10]([CH2:50][OH:51])([CH2:11][O:12]2)[C@@H:9]([OH:8])[C@H:15]([OH:16])[C@H:14]3[OH:24])=[CH:34][C:35]=1[CH2:40][C:41]1[CH:42]=[CH:43][C:44]2[O:48][CH2:47][CH2:46][C:45]=2[CH:49]=1

Participants

4

Reactant 2

HCID 72391,2-DichlorobenzeneHCID 86685135HCID 86685135, compound

Product 1

HCID 86685136HCID 86685136, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

[(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol 5m (100 mg, 0.14 mmol) was dissolved in 5 mL of mixed solution (THF and MeOH, v:v=1:1), followed by addition of o-dichlorobenzene (208 mg, 1.42 mmol) and Palladium/carbon (10 mg, 10%). The mixture was exchanged with H2 three times and stirred for 1.5 hours, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by thin layer chromatography with developing solvent system A to obtain the title compound (1S,2S,3S,4R,5S)-5-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol 5 (58 mg, white solid), yield: 93.5%. MS m/z (ESI): 435.1 [M+1]; 1H NMR (400 MHz, CD3OD): δ 7.47 (d, 1H), 7.39-7.35 (m, 2H), 7.04 (s, 1H), 6.93 (d, 1H), 6.62 (d, 1H), 4.50 (t, 2H), 4.17 (d, 1H), 4.03 (s, 2H), 3.88-3.79 (m, 2H), 3.71-3.65 (m, 2H), 3.62-3.56 (m, 2H), 3.15 (t, 2H).

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by thin layer chromatography with developing solvent system

Sources & evidence

ORD record
ord-bc2e0fe8efd3416eb82f6ac5dea0be51
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

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