HCID 15711866, compound → HCID 54319346, compound

HRID 982107Notes

Reaction equation

HRID 982107 reaction equation
[C:1]([CH:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([OH:13])[C:7]=2[CH2:6][CH:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:4]1)#[N:2].C1C=C[NH+]=CC=1.[Br:26][Br-]Br>C(O)(=O)C>[Br:26][C:9]1[C:8]2[C@H:3]([C:1]#[N:2])[O:4][C@@H:5]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:6][C:7]=2[C:12]([OH:13])=[CH:11][CH:10]=1

Participants

3

Reactant 1

HCID 15711866HCID 15711866, compound2×

Product 1

HCID 54319346HCID 54319346, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 0.94 g (3.8 mmol) of 1-cyano-3,4-dihydro-5-hydroxy-3-phenyl-1H-2-benzopyran, the product of Step 3 of Example 89 in 10 mL of glacial acetic acid was treated with a solution of 1.2 g (3.8 mmol) of pyridine hydrobromide perbromide in 50 mL of glacial acetic acid and the resultant mixture was stirred for 48 h at ambient temperature. The precipitate was filtered to afford 351 mg (28% yield) of the title compound. An additional 229 mg (18% yield) of the desired product precipitated from the filtrate after concentration in vacuo, to give a total of 580 mg (46% yield) of [1R,3R] 8-bromo-1-cyano-3,4-dihydro-5-hydroxy-3-phenyl-1H-2-benzopyran.

Workup

  1. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-7d014d1e7eb14fe18613170c7faff3f8
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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