4-(Adamantan-1-ylmethoxy)-3-bromobenzonitrile → 4-(Adamantan-2-ylmethoxy)-3-cyclopropylbenzonitrile

HRID 1427889Notes

Reaction equation

HRID 1427889 reaction equation
[C:1]12([CH2:11]OC3C=CC(C#N)=CC=3Br)CC3CC(CC(C3)[CH2:2]1)C2.[CH:22]12[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH:23]1[CH2:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][C:35]=1Br)[CH2:29]2>>[CH:22]12[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH:23]1[CH2:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][C:35]=1[CH:11]1[CH2:1][CH2:2]1)[CH2:29]2

Participants

3

Reactant 2

HCID 867028434-(Adamantan-1-ylmethoxy)-3-bromobenzonitrileHCID 867029164-(Adamantan-2-ylmethoxy)-3-bromobenzonitrile

Product 1

HCID 867029154-(Adamantan-2-ylmethoxy)-3-cyclopropylbenzonitrile

Procedure

Following the procedure as described in Example 39 step 1 and making variation as required to replace 4-(adamantan-1-ylmethoxy)-3-bromobenzonitrile with 4-(adamantan-2-ylmethoxy)-3-bromobenzonitrile the title compound was obtained as a colorless solid (0.68 g, 84%): MS (ES+) m/z 308.3 (M+1).

Sources & evidence

ORD record
ord-d82ddd7bc40746d2be6d5140eab7fc8a
Source dataset
uspto-grants-2015_01
Patent number
US08933236B2

Reaction notes

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