Hydrogen Bromide → HCID 14625432, compound

HRID 1380071Notes

Reaction equation

HRID 1380071 reaction equation
C(C1C=CC=CC=1O)#N.[C:10]([C:12]1[CH:26]=[CH:25][CH:24]=[CH:23][C:13]=1[O:14][CH2:15][C@@H:16]1[CH2:20][O:19][C:18](C)([CH3:21])[O:17]1)#[N:11].CCO.[BrH:30]>C(O)(=O)C>[C:10]([C:12]1[CH:26]=[CH:25][CH:24]=[CH:23][C:13]=1[O:14][CH2:15][C@@H:16]([O:17][C:18](=[O:19])[CH3:21])[CH2:20][Br:30])#[N:11]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 702Ethanol2×HCID 119072-HydroxybenzonitrileHCID 14625429HCID 14625429, compound

Product 1

HCID 14625432HCID 14625432, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In the same way as in [H] but reacting 2-cyanophenol (7.1 g, 59.7 mmoles) with (S)-(+)-2,2-dimethyl-4-toxyloxymethyl-1,3-dioxolane (J. Org. Chem. 42, 1006 (1977)) (17.1 g, 59.7 mmoles) the (R)-(-)-4-(2-cyanophenoxymethyl)-2,2-dimethyl-1,3-dioxolane with [α]D (C=1, EtOH)=-30.18°, was obtained. The reaction of this compound (13.9 g, 59.6 mmoles) with 40% hydrobromic acid in acetic acid yields (R)-(-)-3-(2-cyanophenoxy)-2-acetoxy-1-bromopropane with [α]D (C=1, EtOH)=-15.9°.

Workup

  1. customwas obtained

Sources & evidence

ORD record
ord-655946b18d0745e6b809e457bb68941b
Source dataset
uspto-grants-1986_04
Patent number
US04579861

Reaction notes

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