Triphenylphosphine → HCID 16655467, compound

HRID 2116093Notes

Reaction equation

HRID 2116093 reaction equation
[Br:1][CH2:2][C@@H:3]([OH:13])[CH2:4][C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>>[Br:1][CH2:2][C@H:3]1[CH2:4][C:5]2[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=2[O:13]1

Participants

4

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 16655411HCID 16655411, compound

Product 1

HCID 16655467HCID 16655467, compoundYield 76%

Procedure

Treatment of (S)-2-(3-bromo-2-hydroxy-propyl)4-fluoro-phenol (1.97 g, 8 mmol), triphenylphosphine (5.2 g, 20 mmol), and diethylazodicarboxylate (3.11 ml, 20 mmol) generally according to the procedure described for Intermediate 18 afforded 1.40 g (76%) of (R)-2-bromomethyl-5-fluoro-2,3-dihydro-benzofuran as a colorless oil. HRMS ESI m/e 228.9661 [M−H]−. [α]D25=−33.0 (c 1% in methanol).

Sources & evidence

ORD record
ord-e6e149a1bce2461db4949f0f5fea8d50
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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