Carbon tetrabromide → HCID 67416796, compound

HRID 2035397Notes

Reaction equation

HRID 2035397 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@H:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C@@H:12]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[C@H:11]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=3)[CH:10]([CH2:44][O:45][CH2:46][C:47]3[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=3)[O:9]2)=[CH:4][C:3]=1CO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:76]([Br:80])(Br)(Br)Br>O1CCCC1>[Br:80][CH2:76][C:3]1[CH:4]=[C:5]([C@H:8]2[C@@H:13]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)[C@@H:12]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[C@H:11]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=3)[CH:10]([CH2:44][O:45][CH2:46][C:47]3[CH:48]=[CH:49][C:50]([O:53][CH3:54])=[CH:51][CH:52]=3)[O:9]2)[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67418345HCID 67418345, compound

Product 1

HCID 67416796HCID 67416796, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the product from step D (0.36 g, 0.46 mmol) in tetrahydrofuran (5.0 mL) at 0° C. was added triphenylphosphine (0.36 g, 1.38 mmol), followed by dropwise addition of a solution of carbon tetrabromide (0.46 g, 1.38 mmol) in tetrahydrofuran (5.0 mL). The reaction mixture was allowed to warm to room temperature and stirred for 8 hours. The reaction solution was then quenched by addition of methanol and stirred for 15 minutes at room temperature. The resultant mixture was concentrated to dryness and the residue obtained was purified by flash column chromatography (eluent: hexanes/ethyl acetate 95:5 to 60:40) to give (2S,3R,4R,5R)-2-(3-(bromomethyl)-4-chlorophenyl)-3,4,5-tris(4-methoxybenzyloxy)-6-((4-methoxybenzyloxy)methyl)tetrahydro-2H-pyran (0.31 g, partial pure) as a light yellow oil, which was used in the next step without further purification.

Workup

  1. customThe reaction solution was then quenched by addition of methanol
  2. stirringstirred for 15 minutes at room temperature
  3. concentrationThe resultant mixture was concentrated to dryness
  4. customthe residue obtained
  5. customwas purified by flash column chromatography (eluent: hexanes/ethyl acetate 95:5 to 60:40)

Sources & evidence

ORD record
ord-4e68f4d9444f4bd6ad2fa690d467aa76
Source dataset
uspto-grants-2013_11
Patent number
US08575114B2

Reaction notes

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