Carbon tetrabromide → HCID 14842661, compound

HRID 893058Notes

Reaction equation

HRID 893058 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[C@H:10]1[CH2:14][C@@H:13](O)[CH2:12][N:11]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:1]([O:8][C:9](=[O:23])[C@H:10]1[CH2:14][C@H:13]([Br:25])[CH2:12][N:11]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 7408209HCID 7408209, compound

Product 1

HCID 14842661HCID 14842661, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The alcohol 34 (5.34 g, 16.7 mmol) and CBr4 (16.6 g, 50 mmol) were dissolved in 100 mL dichloromethane and solid triphenylphosphine (13.1 g, 50 mmol) was added over a 10 min period. This solution was allowed to stir for 18 h then worked up and purified as for the synthesis of 4a. This gave 4.73 g (74% yield) of the title compound. This material crystallized on standing to give material of m.p.=87°-88° C. (Et2O/hexane). 1H NMR (CDCl3) δ 1.35/1.46 (2s, 9H), 2.41 (m, 1H), 2.58 (m, 1H), 3.90 (m, 2H), 4.48 (m, 2H), 5.19 (m, 2H), 7.34 (s, 5H).

Workup

  1. custompurified as for the synthesis of 4a

Sources & evidence

ORD record
ord-4f340fc51167440a9cbea29bb13e0bdd
Source dataset
uspto-grants-1992_06
Patent number
US05120859

Reaction notes

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